IL44555A - Pyrimidyl (thio)phosphoric acid esters - Google Patents
Pyrimidyl (thio)phosphoric acid estersInfo
- Publication number
- IL44555A IL44555A IL44555A IL4455574A IL44555A IL 44555 A IL44555 A IL 44555A IL 44555 A IL44555 A IL 44555A IL 4455574 A IL4455574 A IL 4455574A IL 44555 A IL44555 A IL 44555A
- Authority
- IL
- Israel
- Prior art keywords
- compositions
- insecticidal
- active ingredient
- diluent
- compounds
- Prior art date
Links
- -1 Pyrimidyl (thio)phosphoric acid esters Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 30
- 241000607479 Yersinia pestis Species 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 11
- 230000000749 insecticidal effect Effects 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000002917 insecticide Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010061217 Infestation Diseases 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008262 pumice Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- CWLLGCJZWOJVPK-UHFFFAOYSA-N 2-(dimethylamino)-6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound CN(C)C1=NC(=O)C=C(C(F)(F)F)N1 CWLLGCJZWOJVPK-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- HAEVLZUBSLBWIX-UHFFFAOYSA-N 2-octylphenol;oxirane Chemical compound C1CO1.CCCCCCCCC1=CC=CC=C1O HAEVLZUBSLBWIX-UHFFFAOYSA-N 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000131102 Oryzaephilus Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 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
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
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
BYRIMIDYL(THIO)PHOSPHORIC ACID ESTERS 'mads ( i »n) nsonn © D»TODS TS' S This invention relates to novel organophosphorus compounds, processes for their preparation, compositions comprising them and methods of combating insect pests using them.
Israel Patents Nos.21035 and 32701 disclose the use of certain classes of pyrimidinyl esters of phosphorus as insecticides. However their continued use at a locus may induce a build up of resistant strains of the insects. It is therefore useful to provide alternative insecticides which might be used to counter the build up of resistant strains, and the compounds of this invention represent such alternative insecticides .
Accordingly the present invention provides compounds of formula X wherein X is oxygen or sulphur; Y and 2 are lower alkoxy con- 1 2 taining from one to four carbon atoms; R and R are lower 3 alkyl containing from one to four carbon atoms; and R s hydrogen or halogen.
In a preferred aspect the invention provides compounds of the above formula wherein X is oxygen or sulphur; Y and Z are both methoxy or ethoxy; and R and R are both methyl 3 or ethyl; and R is hydrogen or chlorine.
Specific examples of compounds accordingto the invention include those givenin Table 1 below wherein the values of R , 2 3 R , R , X Y and Z are set out.
TABLE 1 The invention compounds may be prepared by the process of treating a compound of formula :- or an alkali metal salt thereof, with a compound of formula :- X I! Y-P-Q Z wherein Q is a halogen atom, preferably a chlorine 1 2 or bromine atom, and R , R , R , X, Y and Z have any of the meanings given hereinbefore.
The above preparation may be carried out in a non-reacting diluent or solvent and in the presence of a base.
The invention compounds may be used to combat insect pests on their own, but we more conveniently used in the form of a composition comprising the invention compound and also comprising a diluent or carrier.
In a further aspect therefore the present insecticidal invention also provides p«e-ti-e-id-al compositions comprising as an active ingredient a compound of formula:- „ wherein X, Y, Z, R , R and R^ have any of the meanings given hereinbefore, in association with a diluent or carrier.
In a preferred aspect the invention provides insecticidal pe¾-ti-d-tial compositions comprising as an active ingredient any of the compounds set out in Table I herein, in association with a diluent or carrier.
The compositions may be in the form of granular powders wherein the active ingredient is absorbed on a porous granular material, for example pumice.
Alternatively the compositions may be in the form of liquid preparations to be used as dips or sprays, which are generally aqueous dispersions or emulsions of the active ingredient in the presence of one or. more known wetting agents, dispersing agents or emulsifying agents . These compositions are prepared by dissolving the active ingredient in a suitable solvent, for example, a ketonic solvent such as diacetone alcohol, and adding the mixture so obtained to water which may contain one or more known wetting, dispersing or emulsifying agents.
The compositions which are to be used in the form of aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient or ingredients, the said concentrate to be diluted with water before use. These concentrates are often required to withstand storage for prolonged periods and after such storage, to be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
The concentrates may contain 10-85 by weight of the active ingredient or ingredients. When diluted to form aqueous preparations, such preparations may contain varying amounts of the active ingredient depending upon the purpose for which they are to be used.
For agricultural or horticultural purposes, an aqueous preparation containing between 0.0001% and 0.1% by weight of the active ingredient or ingredients may be used.
The compositions of the present invention, may, if desired, also comprise in addition to a compound of the present invention, at least one other biologically-active ingredient, for example an insecticide, or a fungicide.
In use the compositions are applied to the pests, to the locus of the pests, to the habitat of the pests, or to growing plants liable to infestation by the pests, by any of the known means of applying pesticidal compositions, for example by dusting or spraying.
The compounds of the invention and compositions comprising them are very toxic to wide varieties of insect and other invertebrate pests, including, for example, the following :-Tetranychus telarius (red spider mites) Aphis fabae , (aphids) Megou a viceae (aphids) Aedes aegypti (mosquitos) Musea domestlca (houseflies ) Pieris brassicae (white butterfly, larvae) Plutella maculipennis (diamond back moth, larvae) Phaedon cochleariae (mustard beetle)) Calandra granaria (grain beetle) The invention is illustrated by the following examples.
EXAMPLE 1 5 Parts by weight of Compound No.l of Table 1 were thoroughly mixed in a suitable mixer with 95 parts by weight of talc. There was thus obtained a dusting powder.
EXAMPLE 2 10 Parts by weight of Compound No.2 of Table 1 10 parts of an ethylene oxide-octylphenol condensate ("Lissapol" NX; "Lissapol" is a Trade Mark) and 80 parts by weight of diacetone alcohol were thoroughly mixed. There was thus obtained a concentrate which, in mixing with water, gave an aqueous dispersion suitable for application as a spray in the control of insect pests.
EXAMPLE 3 A granular composition was prepared by dissolving the active ingredient in a solvent, spraying the solution obtained on to the granules of pumice and allowing the solvent to evaporate. % wt.
Compound No.3 of Table 1 5 Pumice Granules 95 100% EXAMPLE 4 An aqueous dispersion formulation was prepared by mixing and grinding the ingredients recited below in the proportions stated. % wt.
Compound No.4 of Table 4 i»0 Calcium lignosulphonate 10 Water 50 10035 EXAMPLE 5 The activity of a number of the compounds was tested against a variety of insect and other invertebrate pests. The compounds were used in the form of a liquid preparation containing 0.1% by weight of the compound except in the test with Aedes aegypti where the preparations contained 0.01% by weight of the compound. The preparations were made by dissolving each of the compounds in a mixture of solvents consisting of parts by volume of acetone and 1 part by volume of diacetone alcohol. The solutions were then diluted with water containing 0.01$ by weight of a wetting agent sold under the trade name "LISSAPOL" NX until the liquid preparations contained the required concentration of the compound "Lissapol" is a Trade Mark.
The test procedure adopted with regard to each pests was basically the same and comprised supporting a number of the pests on a medium which was usually a host plant or a foodstuff on which the pests feed, and treating either or both the pests and the medium with the preparations.
The mortality of the pests was then assessed at periods usually varying from one to three days after the treatment.
The results of the tests are given below in Table 2. In this table the first column indicates the name of the pest species. Each of the subsequent columns indicates the . host plant or medium on which it was supported, the number of days which were allowed to elapse after the treatment before assessing the mortality of the pests, and the results obtained for each of the compounds, numbered as in Table I above. The assessment is expressed in integers which range from 0-3. 0 represents less than 30$ kill 1 represents 30-49$ kill 2 represents 50-90$ kill 3 represents over 90 kill A dash(-) in Table 2 indicates that no test was carried out.
TABLE 2 In the foregoing Table "contact test" indicates that both the pests and the medium were treated, and "residual test" indicates that the medium was treated before infestation with the pests EXAMPLE 6 This example illustrates the preparation of 0,0-diethyl 2-dimethylamino-M-trifluoromethylpyrimidin 6-yl phosphate (Compound No. 3, Table 1) having the formula :- A mixture of 2-dimethylamino-l»-trifluoromethyl-6-hydroxypyrimidine (3.1 g) , anhydrous potassium carbonate (2.8 g) , and dry ethyl acetate (50 ml) was refluxed together for 1 hour and then cooled to about 0°C. Diethylphosphorochloridate (2.5M g) was then added dropwise to the stirred mixture and when the addition was complete the mixture was re luxed for sixteen hours, after which it was allowed to cool to the ambient temperature. After filtration to remove the solids present, the filtrate was washed with water (2 x 50 ml), 10J6 w/v aqueous sodium hydroxide solution (1 x 50 ml), and finally with water until the washings were neutral. The ethyl acetate solution was dried over anhydrous magnesium sulphate, and after filtering, the the solvent was evaporated under reduced pressure to yield a residual pale yellow oil, which on cooling and scratching yielded crystalline 0,0-diethyl 2-dimethylamino-4-tri fluoromethylpyrimidin-6-yl phosphate, melting point 22-24°C.
EXAMPLE 7 By a process similar to that illustrated in Example 6 each of the compounds numbered 1,2,4,5 and 6 in Table 1 was prepared from the appropriate starting materials, thus: 0,0-dimethyl 2-dimethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate (Compound No.l, Table 1) was prepared from 2-dimethylamino- -trifluoromethy1- 6-hydroxypyrimidine and diethylphosphorochloridothionate 2^ and had a refractive index of N^ l 4940 0.0-diethyl 2-dimethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate (Compound No.2, Table 1) was prepared from 2-dimethylamino-4-trifluoromethyl- 6-hydroxypyrimidine and diethyIphosphorochloridothionate 20 and had a refractive index of ND 1.4860; 0,0-Diethyl 2-diethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate (Compound No. , Table 1) was prepared from 2-diethylamino-4-trifluoromethyl-6-hydroxyprimidine and dieth Iphosphorochloridothionate , and had a melting point 25-27°C. 0,0-Dimethyl 2-diethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate (Compound No,5 Table 1) was prepared from diethylamino-4-trifluoromethyl- 6-hydroxyprimidine and dimethylphosphorochloridothionate , and had a melting point of 27-29°C; and 0,0-Diethyl 2-dimethylamino-5-chloro-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate was prepared from 2-dimethylamino-5-chloro-4-tri luoromethyl-6-hydroxy-pyrimidine and diethylphosphorochloridothionate , and had a melting point of 30-32°C.
Claims (1)
1. Compounds of formula :- lower wherein X is oxygen or sulphur; Y and Z are/alkoxy containing from one to four carbon atoms; R1 and R lower are /alkyl containing from one to four carbon atoms, and R^ is hydrogen or halogen. Compounds of formula wherein X is oxygen or sulphur;, Y and Z are both 1 2 methoxy or ethoxy; R and R are both methyl or ethyl and R^ is hydrogen or chlorine. 3. 0,0-Dimethyl 0-2-dimethylamino-i|-trifluoromethyl-pyrimidin-6-yl phosphorothionate. . 0,0-Diethyl 0-2-dimethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate. 5. 0,0-Diethyl 0-2-dimethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphate. 6. 0,0-Diethyl 0-2-diethylamino-^-trifluoromethyl-pyrimidin-6-yl phosphorothionate . 7. 0,0-Dimethyl 0-2-diethylamino-4-trifluoromethyl-pyrimidin-6-yl phosphorothionate. 8. 0,0-Diethyl 0-2-dimethylamino-5-chloro-1-trifluoro-methylpyrimidin-6-yl phosphorothionate . 9. Process for the preparation of compounds according to claim 1 which comprises treating a compound of ormula :- FT OH or an alkali metal salt thereof, with a compound of formula:- X II Y-P-Q I z 1 2 "¾ wherein Q is a halogen atom and R , R , R , X, Y and Z have any of the meanings given in Claim 1. 10. Process as claimed in claim 9 wherein Q is chlorine or bromine. i 11. Process as claimed in either of claims 9 and 10 carried out in a non-reacting solvent or diluent. 12. Process as claimed in claim 11 wherein the solvent or diluent is ethyl acetate. 13· Process as claimed in any of claims 9 to 12 carried out in the presence of a base. 1 . Process as claimed in claim 13 wherein the base is potassium carbonate. Insecticidal 15. -E-®stio-idai. compositions comprising as an active ingredient a compound of formula :- wherein X, Y, Z, R , R and R^ have any of the meanings given in claim 1, in association with a diluent or carrier. Insecticidal 16. - sfe-i-oidai compositions comprising as an active ingredient any of the compounds claimed in any of claims 3 to 8. Insecticidal 17. -P-e-sti-c-fkal compositions as claimed in either of claims 15 and 16 comprising at least one wetting, dispersing, or emulsifying agent. Insecticidal 18. P-ss- cidal- compositions as claimed in any of claims 15 to 17 wherein the diluent or carrier is a liquid diluent. Insecticidal 19· P-ee-t-ie-i-d- l compositions as claimed in either of claims 15 and 17 wherein the diluent or carrier is a solid diluent or carrier. Insecticidal . , . „ . , . , . 20. P-ee-t-iei-ddi- compositions as claimed in claim 19 wherein the carrier is a porous granular material. ITis©c"ticid9.1 21. P-ee-tieiial compositions as claimed in any of claims 15 to 20 comprising from 10-85¾ by weight of the active ingredient. 22. compositions as claimed in any of claims 15 to 20 comprising from 0.0001$ to 1.01 b weight. of the active ingredient. Insecticidal 23. f* s-ti-c-idai compositions as claimed in any of claims 15 to 22 comprising at least one other biologically active ingredient. Insecticidal 24. •Fe-sfci-e-idal compositions as claimed in claim 23 wherein the other biologically active ingredient is an insecticide. Insecticidal 25. i^s i-cirdai- compositions as claimed in claim 23 wherein the other biologically active ingredient is a fungicide. 2$. A method of combating pes e which comprises applying to the pests themselves, or to the locus of the pests, or to the habitat of the pests., or to growing plants liable to infestation by the pests, ixi s ec t c i dfl 1 a-pee-fc-ie -da-l composition as claimed in any of claims 15 to 25.. 27. Compounds, as claimed in claim 1, processes for
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2520773A GB1409202A (en) | 1973-05-25 | 1973-05-25 | Fluorine-containing organo-phosphorus esters having pesticidal properties |
Publications (2)
Publication Number | Publication Date |
---|---|
IL44555A0 IL44555A0 (en) | 1974-06-30 |
IL44555A true IL44555A (en) | 1977-01-31 |
Family
ID=10223960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL44555A IL44555A (en) | 1973-05-25 | 1974-04-03 | Pyrimidyl (thio)phosphoric acid esters |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS5046841A (en) |
CH (1) | CH585016A5 (en) |
DE (1) | DE2425237A1 (en) |
FR (1) | FR2230651B1 (en) |
GB (1) | GB1409202A (en) |
IL (1) | IL44555A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3528264A1 (en) * | 1985-08-07 | 1987-02-12 | Bayer Ag | PHOSPHORUS (PHOSPHONE) ACID ESTER |
DE3542173A1 (en) * | 1985-11-29 | 1987-06-04 | Basf Ag | PHOSPHORIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING Pests |
DE3914714A1 (en) * | 1989-05-04 | 1990-11-22 | Bayer Ag | PYRIMIDINYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) ACID (AMID) ESTER |
DE19917785A1 (en) * | 1999-04-20 | 2000-10-26 | Bayer Ag | New 2,4-diamino-pyrimidine derivatives useful as microbicides in protection of plants and materials and as herbicides |
-
1973
- 1973-05-25 GB GB2520773A patent/GB1409202A/en not_active Expired
-
1974
- 1974-04-03 IL IL44555A patent/IL44555A/en unknown
- 1974-05-21 JP JP49056199A patent/JPS5046841A/ja active Pending
- 1974-05-24 DE DE19742425237 patent/DE2425237A1/en active Pending
- 1974-05-24 CH CH714374A patent/CH585016A5/xx not_active IP Right Cessation
- 1974-05-24 FR FR7418098A patent/FR2230651B1/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AU6937974A (en) | 1975-11-27 |
JPS5046841A (en) | 1975-04-25 |
FR2230651B1 (en) | 1977-10-14 |
IL44555A0 (en) | 1974-06-30 |
FR2230651A1 (en) | 1974-12-20 |
DE2425237A1 (en) | 1974-12-12 |
GB1409202A (en) | 1975-10-08 |
CH585016A5 (en) | 1977-02-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
PL84208B1 (en) | ||
US3686200A (en) | Phosphoric acid esters | |
US4041157A (en) | Fungicidal pyrimidine derivatives | |
US3657247A (en) | Pesticidal halogen-substituted pyrimidinyl phosphorus esters | |
US4014882A (en) | Trifluoromethyl substituted pyrimidine derivatives useful as insecticides | |
US3629474A (en) | Insecticidal and fungicidal compositions and methods of combating fungi and insects using isoxazolyl carbamates | |
IL44555A (en) | Pyrimidyl (thio)phosphoric acid esters | |
US3932631A (en) | Certain organophosphorus compounds used to control insects | |
US4237168A (en) | N-(4-Chloro-2-methylphenyl)-N-hydroxy methanimidamide and its pesticidal use | |
CA1047497A (en) | Heterocyclic derivative | |
US3767662A (en) | Certain 1,3-thiazolidin-4-ones | |
US4225595A (en) | Piperazine phosphates and phosphonate insecticides | |
GB2055103A (en) | 5-pyrimidinols and phosphorus esters thereof | |
US4048172A (en) | Carbonylmethylpyrimidin-6-yl phosphates and phosphorothionates | |
US3325492A (en) | Thiophosphoric (-phosphonic, -phosphinic) or dithiophosphoric (-phosphonic, -phosphinic) acid esters | |
US3551529A (en) | Di-lower alkyl phosphites of 2-(lower-alkylthio)alkanaldoximes | |
US4439430A (en) | O,O-Diethyl O-[(p-tertiarybutylthio)phenyl]phosphorothioates and its insecticidal use | |
US3705914A (en) | Pesticidal carbamate derivatives of naphthaquinones | |
US3935212A (en) | Pesticidal substituted 2-hydroxylaminopyrimidinyl phosphorus esters | |
US4424217A (en) | Substituted phenyl phosphorothioates and their use as pesticides | |
DE69117310T2 (en) | Biphosphorylhydrazine and its use as pesticides | |
US3551562A (en) | Insecticidal use of s-((4-oxo-1,2,3-benzotriazin - 3(4h)-yl) - methyl) phosphorothioates and phosphorodithioates | |
US3843655A (en) | Heterocyclic compounds and compositions | |
US3151022A (en) | Omicron, omicron-dimethyl-omicron-(4-methylmercaptophenyl) phosphate and pesticidal use | |
US3502670A (en) | S-((4-oxo - 1,2,3-benzotriazin-3(4h)-yl)-methyl) phosphorothioates and phosphorodithioates |