CA1048047A - Esters - Google Patents

Esters

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Publication number
CA1048047A
CA1048047A CA162,024A CA162024A CA1048047A CA 1048047 A CA1048047 A CA 1048047A CA 162024 A CA162024 A CA 162024A CA 1048047 A CA1048047 A CA 1048047A
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CA
Canada
Prior art keywords
formula
group
compound according
carbon atoms
parts
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
Application number
CA162,024A
Other languages
French (fr)
Other versions
CA162024S (en
Inventor
Jozef Drabek
Paul L. Valint
Alexis A. Oswald
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CH122672A external-priority patent/CH569415A5/en
Priority claimed from CH1460072A external-priority patent/CH576232A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Application granted granted Critical
Publication of CA1048047A publication Critical patent/CA1048047A/en
Expired legal-status Critical Current

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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

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

Compounds of the formula (I)

Description

`^ -The present invention relates to thiophosphoric acid phenyl esters having pesticidal properties.
According to the present invention there are provided Compounds of the formula (I) R 0\10 ~ R2 (I) wherein R represents a~me~hyl or ethyl group, Rl represents a C3-C5-alkyl group, R2 represents an alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl group having at most 5 carbon atoms in toto or a group of the formula -S(CH2)mCN~ -SO(CH2)mCN~ -S(CH2)mCl~ -SO(CH2)mCl, SCC13, SOCC13, S(CH2)mCOOR3, -SO(CH2)mCOOR3, ~S(CH2)mCON(R4)R5 or -SO(CH2)mCON~R4)R5 wherein R3 represents an alkyl group having at most 4 carbon atoms, R4 and R5 independently of one another represent~a hydrogen atom or an alkyl group having at most 4 carbon atoms and m represents the integer 1 or 2; and Xl ~nd X2 independently of one another represent a hydrogen or halogen atom or an alkyl group having at most 4 carbon atoms.
By halogen is meant fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
The alkyl groups and moieties within the definitions of Rl to R5 may be straight-chain or branched. Examples of such groups or moieties are as appropriate to the definitions: methyl, ethyl, propyl, isopropyl and n-~
i-, sec. and tert. butyl.
Rl in the compounds of formula I preferably represents an n-propyl, i-propyl, i-butyl, sec.-butyl, or n-pentyl group. Most preferably R repre-sents an ethyl group and ~ represents an n-propyl group.

Preferably R2 represents a group of the formula -SCH2CN3 -SOCH2C~ -SCH2Cl, SOCH2Cl, -SCC13, -SOCC13, -SCH2COOR3, -SOCH2COOR3, -SCH2CON \ or -SOCH2CON \ (wherein R3 represents a methyl or ethyl group and R4 and ~5 independently of one another represent a hydrogen atom or methyl group); especially a group of the formula -SC}l2CN, -SCH2Cl, -scH2cooc2Hs~ or -ScH2co 2 R2 may also suitably represent an alkylthiomethyl, alkylsulphinyl-methyl or alkylsulphonylmethyl group containing at most 4 carbon atoms in the said alkyl moiety; preferably a methylthiometh~l, methylsulphinylmethyl or methylsulphonyl~et~yl group.
Preferably X, and X2 each represents a chlorine or bromine atom or a methyl group.
The compounds of formula I can be manufactured by the following processes which are analogous to those known in the art;

la) RO O R
> p _ Cl + HO ~ 2 acid binding 1 ~ ~1 agent (II) X2 (III) lb) R ~ O ~ ~eO ~ 1 -D

RlS X
(II~ (IV) ~8~7
2) \ P-Cl -~ H0 ~ acid binding \ ~ ~ R2 (V) x2 (VI) (X)n R0 0 acid binding \!1_o /9~R2 -~ HSR
/ ~\ ~ (VII) agent Cl ~
(VI) X2 (VIII) 10R0 > S ~ ( 3)3 (X) R30C~--SMe S (XI) ~ ~Hal or >
MeSR3 ~(XII) (XIV) or Me2S l(XIII) In the formulae II to XIV, R, Rl, R2, Xl and ~2 have the meanings given for the formula I, Me represents an alkali metal ( in particular sodium or potassium~ or ammonium or alkyl-ammoniumion~ R3 represents hydrogen or alkyl with 1 to 4 carbon atoms and Hal represents a halogen atom, such as chlorine, bromine or iodine.
Suitable acid binding agents are: tertiary amines, e.g.
trialkylamines, pyridine, dialkylanilines; inorganic bases, such as hydrides, hydroxides; carbonates and bicarbonates of alkali and alkaline earth metals.
During the reactions it is sometimes necessary to use a catalyst~ for example copper or copper chloride. Processes 1~ 2, and 3 can be carried out at normal pressure and in solvents or diluentsO

~4~ L7 EXamples of suitable solvents or diluents are: ether and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, tetra~
hydrofuran; amides, such as N,N-dialkylated carboxylic acid amides; aliphaticg aromatic and halogenated hydrocarbons, in particular benæene, toluene, xylenes, chloroform, chlorobenzene3 nitriles, such as acetonitrile; dimethyl sulphoxide; alcohols, such as ethanol and ketones~ such as acetone, ethyl methyl ketone, water.
The starting materials of the formulae, II~ III, IV, V and IX
are known or may be manufactured in analogous manner to known methods, e.g.
those described in German Auslegeschriften 1051863, 1063177, 1088980 or i298990.
The active substances of the formula I are suitable for combatting pests of the class Insecta or of the order Acarina. Thus the compounds of formula I surprisingly have markedly better action against all development stages, e.gO eggs~ larvae, pupae, nymphs and adults, of insects and repre-sentatives of the order Acarina, such as mites andticks than e.g. analogous compounds of German patent 1138041. Thus the compounds of the formula I can be used against insects of the families:
Tetti~oniidae Tenebrionidae 5~ Chrysomel_ ae E~ Bruchidae BIattidae Tineidae Reduviidae Noctindae Pyrrhocoridae Lymatriida Cimicidae Pyralidae Delphacidae Culicidae Aphididae ~
Diaspididae Stomoxydae PseudocQccidae Trypetidae Scarabaeldae Muscidae Dermestidae Calliphoridae and Coccinellidae Pulicidae Acarida of the families:
Ixodidae Argasidae and Dermanyssidae.
The insecticidal a~d/or acaricidal action can be substantially broadened and adapted to suit the particular circumstances by the addition of other insecticides and/or acaricides.
The compounds of the formula I may be used as pure active substance or together with suitable carriers and/or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances convention-ally used in formulation technique~such, for example, as solvents, dispersants, wetting agents, adhesives, thickeners, binders and/or fertilisers.
For application~ the compounds of the formula I may be processed to dusts, emulsion concentrates~ granules~ dispersions, sprays~ to solutions, or suspensions inîthe conventional formulation which is commonly employed in application technology. Mention may also be made of cattle dips and spray races, in which aqueous preparations are used.
The agents according to the invention are manufactured in known manner by intimately mixing and/or grinding active substances of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active substances. The active substances may take, and be used in the following forms:
Solid forms:
Dusts, tracking agents, granules~ coated granules, impregnated granules and homogeneous granules.
Liquid forms:
a) active substances which are dispersible in water: wettable 8~
powders, pastes, emulsions;
b) solutions.
The active substances of the formula I can, for example, be formulated as follows;
Dusts The following substances are used to manufacture a) a 5% and b) a 2% dust:
a) 5 parts of active substance parts of taleum b) 2 parts of active substance 1 part of highly disperse silicic acid 97 parts of talcum.
The active substances are mixed with the carriers and ground.
Granules The following substances are used to produce 5% granules:
5 parts of active substance, 0.25 parts of epichlorohydrin, 0.25 parts of cetyl polyglycol ether,
3.~0 parts of polyethylene glycol, 91 parts of kaolin (particle si~e 0.3 - 0.8 mm).
The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone; the polyethylene glycol and cetyl polyglycol ether are then added~ The thus obtained solution is sprayed on kaolin, and the acetone subsequently evaporated in vacuo.
~ettable powder:
The following constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d3 a 10% wettable powder:
a) 40 parts of active substance, 5 parts of sodium lignin sulphonate, ~4~ 7 1 part of sodium dibutyl~naphthalene sulphonate, 54 parts of silicic acid.
b) 25 parts of active substance,
4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mix~ure (1:1), 1.5 parts of sodium dibutyl naphthalene sulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalkg 28.1 parts of kaolin.
c) 25 parts of active substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 16.5 parts of kieselguhr, 46 parts of kaolin.
d) 10 parts of active substance, 3 parts of a mixture of the sodi~ salts of saturated fatty alcohol sulphates,
5 ~cparts of naphthalenesulphonic acid/formaldehyde condensate, 82 parts o~ kaolin.
The active substances are intimately mixed, in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to give suspensions of an~ desired concentration.
~sifiable concentrates^
The following substances are used to produce a) a 10% and b) a 25% emulsifiable concentrate:
a) 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, ~L~4~7 3.4 parts of a combination emulsifier consisting of fatty alcohol polyglycol ether and alkylarylsulphonate calcium saltg parts of dimethylformamide, 43~2 parts of xylene.
b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, parts of an alkylarylsulphonate/fatty alcohol-polyglycol ether mixture, parts of dimethylformamide, 5?~5 parts of xylene.
From these concentrates it is possible to produce, by dilution with water, emulsions of any desired concentration.
Spray:
~

The following constituents are used to prepare a 5% spray:
5 parts of active substance, 1 part of epichlorohydrin~
94 parts of benzine (boiling limits 160 - l90 C).
Example 1 0-ethyl-5-n-propyl-0-(4-methylmerca~to-phenyl~-thiophosph_te 12.2 g of triethylamine are added to a solution of 16.8 g of 4-methyl-mercapto-phenol in 150 ml of benzene. While stirring constantly, 24.4 g of thiophosphoric-0-ethyl-S-n-propyl-ester chloride are added drop-wise at 10 - 15 C0 Stirring is then continued for 12 hours at room temper-ature. The mixture is washed with water, 3% sodium carbonate solution, and again with waterg then dried over anhydrous sodium sulphate. The benzene is distilled off and the residu0 is purified by molecular distillation, to give 27 g of the compound of the formula ~48(~7 2 5\ ~

(n~c3H7s s~3 with a melting point of 125 C/O.OOl Torr; n D = 1.5501. The following compounds are also manufactured in analogous manner:

R S >
6 5 ~9L8~D~7 _ . .

~d u~
~1 ~1 ~1 ~ 11 11 11 R c~

D p~ X ~
..
n . . , _ ~t V ~ ~
~ I ~ X
. _ r~

.
V ~Q V
~ C~ ~ C`~ ~`;i ., ,~
r~
~:~ 3 .
U~
0:;

_ _ _ ~_ -~4~3~47 . ~ _ .. = .. ,..... ...
.
,~ o u~
U~

R C~f~ C`15 fl C`
. __ . _ _ ~D ~
. ., . . , _ I
U~ ~ X ~ C
_ I

~ ~ 0 ~ ~
V
.
~ ~ ~T~ V ~ ~ ~
. . _ ..
C~ ~ ~ X ~q X P~
.

~; ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
~ V ~
,,,, ,.,,,,,, . ~ . . _ _ . . ..
X :: ~ X
~; ~ ,~ V~ y~ V~ ,~ V~ y~ y~

3~41~47 ., ___ R
. .__ ~ . . . . _ ,.
~9 ~ X ~: X
U~ ~ C X
. .. ... . , _____ .

~ c~ c~ c~ ~1 ~ C`l C~ ~ ~
I X ~ ~ ~ O
~ ~ a a ~ ~ ~
~ .
~ O

. . . . ... ..
~ I d _I ~ ~ ~ ~ ~ ``~
~; ~ X ~ ~ !r ~ C ~ X~ ~-2z ~ ~ ~ ol~ ~ o Example 2 Insecticidal ingest ~oison action Tobacco and potato plants were sprayed with a 0.05% aqueous emwl-sion (obtained from a 10% emulsifiable concentrate).
A~ter the coating had dried, the tobacco plants were populated with Egyptian cotton leaf worms (Spodoptera literalis) and the potato plants with Colorado potatO beetle larvae (~eptinotarsa decemlineata). The test was carried out at 24 C and 60% relative humidity. In the above test, the ` compounds according tocExample I displayed ingest poison action against Spodoptera literalis and Leptinotarsa decemlineata.
Example 3 Six rice plants at a time of the variety Caloro were transplanted into plastic pots (diameter at the top = 17 cm) and reared to a height of about 60 cm~ I~nfestation with Chilo suppressalis larvae (Ll: 3~4 mm long) took place 2 days after the active substance had been applied in granule form to the paddy water (rate of application: 8 kg of active substance per hectare). Evaluation of the insectieidal action took plaee 10 days after application of the granules.
The eompo~ds aceording to Example I were active in the above test against Chilo suppressalis.
ExamF~e 4 Aetion a~ st Aulacophora femoralis, Paehmoda and Chortophila larvae Sterilised eompost earth was homogeneously mixed with a wettable powder containing 25% of aetive substance so that there resulted a rate of application of ~ kg of active substance per hectar~.
Young zucchetti plants (Cucumis pepo) were put into plastic pots with the treated soil ~3 plants per pot; diameter of pot = 7 cm). Each pot was infeeted immediately after~ards with 5 Aulacophora femoralis and Pachmoda i9iV47 or Chortophila larvae. The control was carried out 4, 8, 16 and 32 days after depositing the larvae.
At 80 - 100% kill after the first control, a fresh infestation with 5 larvae each was carried out in the same soil sample with 3 new zucchetti plants. If the activity was less than 80%, the remaining larvae remained in the soil sample until the control immediately following. If an active sub-stance at a rate of application of 8 kg/ha~still effected a 100% kill7 a further control with 4 and 2 kg of active substance per hectare was carried out.
In the above test, the compounds according to Example I displayed action against Aulacophora femoralis, Pachmoda and Chortophila larvae.
Exam~e_5 ction ag_ nst ticks -~) Rhlcephalus burs Five adult ticks and 50 tick larvae were counted into a glass tube and immersed for l to 2 minutes in 2 ml of an aqueous emulsion from an emulsion series each containing lOO~ lO, l and~O.l ppm of test substance.
The tube was then sealed with a standardised cotton wool plug and placed on its head, so that the active substance emulsion could be adsorbed by the cotton wool.
In the oase of the adults evaluation took place after 2 weeks, and in that of the larvae after 2 days. Each test was repeated twice.
B) Boophilus microplus (larvae) Tests were carried out in each case with 20 OP-sensitive larvae using an an~logous dilution series as in the case of test A. (The resistance refers to the tolerability of Diazinon).
The compounds according to Example I acted in these tests against adults and larvae of Rhicephalus bursa and sensitive and OP-resistant larvae of Boophilus microplus.

Example 6 Acaracidal action Phaseolus vulgaris (dwarf beans) have an infested piece of leaf from a mass culture of Tetranychus urticae placed onthem 12 hours before the test for the acaricidal action. The mobile stages which have migrated are sprayed with the e~ulsified tes~ preparations from a chromatography a~omiser so that the spray broth does not run offO The number of living and dead larvae, adults and eggs are evaluated after 2 to 7 days under a stereoscopic microscope and the res~lt expressed in percentages. During the "interim", the treated plants are kept in gr0enhouse compartments at 25 C.
The compounds according to ~xample 1 were ac~ive in the above test against eggs, larvae and adults of Tetranychus urticae.

Claims (22)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Compounds of the formula (I) wherein R represents a methyl or ethyl group, R1 represents a C3-C5 alkyl group, R2 represents an alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl group having at most 5 carbon atoms in toto or a group of the formula -S(CH2)mCN, -SO(CH2)mCN, -S(CH2)mCl, -SO(CH2)mCl, SCC13, SOCC13, -S(CH2)mCOOR3, -SO(CH2)mCOOR3, -S(CH2)mCON(R4)R5 or --SO(CH2)mCON(R4)R5 wherein R3 represents an alkyl group having at most 4 carbon atoms, R4 and R5 independently of one another represent a hydrogen atom or an alkyl group having at most 4 carbon atoms and m represents the integer 1 or 2; and X1 and X2 indepently of one another represent a hydrogen or halogen atom or an alkyl group having at most 4 carbon atoms.
2. Compounds according to claim 1 wherein R1 represents an n-propyl, i-propyl, i-butyl, sec.-butyl, or n-pentyl group.
3. Compounds according to claim 2 wherein R represents an ethyl group and R1 represents an n-propyl group.
4. Compounds according to claim 1 wherein X1 and X2 independently of one another represent hydrogen, chlorine or bromine atom or a methyl group.
5. Compounds according to any one of claims 2 to 4 wherein R2 repre-sents a group of the formula -SCH2CN, -SOCH2CN, -SCH2Cl, SOCH2Cl, -SCC13, -SOCC13, -SCH2COOR3, -SOCH2COOR3, -SCH2CON(R4)R5, or -SOCH2CON(R4)R5 wherein R3 represents a methyl or ethyl group and R4 and R5 independently of one another represent a hydrogen atom or methyl group.
6. Compounds according to any one of claims 2 to 4 wherein R2 represents a group of the formula -SCH2Cl, -SCH2CN, -SCH2COOC2H5 or -S-CH2CONH2.
7. Compounds according to any one of claims 2 to 4 wherein R2 represents an alkylthiomethyl, alkylsulfinylmethyl or akylsulfonylmethyl group.
8. Compounds according to any one of claims 2 to 4 wherein R2 represents a methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl group.
9. The compound according to claim 1 of the formula
10. The compound according to claim 1 of the formula
11. The compound according to claim 1 of the formula
12. The compound according to claim 1 of the formula
13. The compound according to claim 1 of the formula
14. The compound according to claim 1 of the formula
15. The compound according to claim 1 of the formula
16. The compound according to claim 1 of the formula
17. The compound according to claim 1 of the formula
18. The compound according to claim 1 of the formula
19. The compound according to claim 1 of the formula
20. A method of combatting pests of the class Insecta or Acarina at a locus, which comprises applying to said locus a compound as claimed in claim 1.
21. A method according to claim 20 wherein the locus comprises agri-cultural or horticultural crops or plants.
22. A method according to claim 20 or 21, wherein the pests are insects.
CA162,024A 1972-01-26 1973-01-25 Esters Expired CA1048047A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH122672A CH569415A5 (en) 1972-01-26 1972-01-26 Thiophosphate esters - insecticides,acaricides,fungistats and bacteriostats
CH1460072A CH576232A5 (en) 1972-10-05 1972-10-05 Thiophosphate esters - insecticides,acaricides,fungistats and bacteriostats
CH1852872 1972-12-20

Publications (1)

Publication Number Publication Date
CA1048047A true CA1048047A (en) 1979-02-06

Family

ID=27172806

Family Applications (1)

Application Number Title Priority Date Filing Date
CA162,024A Expired CA1048047A (en) 1972-01-26 1973-01-25 Esters

Country Status (13)

Country Link
JP (1) JPS6036403B2 (en)
AT (1) AT319662B (en)
BE (1) BE794503A (en)
CA (1) CA1048047A (en)
DD (1) DD103142A5 (en)
DE (1) DE2303185C2 (en)
ES (1) ES410937A1 (en)
FR (1) FR2169223B1 (en)
GB (2) GB1421562A (en)
HU (1) HU167104B (en)
IL (2) IL41306A (en)
IT (1) IT978469B (en)
NL (1) NL7301018A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5727081B2 (en) * 1974-04-05 1982-06-08
JPS5635166B2 (en) * 1973-07-31 1981-08-15
DE2357526C2 (en) * 1973-11-17 1982-04-22 Bayer Ag, 5090 Leverkusen O-phenylthionothiolphosphoric acid esters, process for their preparation and their use as insecticides and acaricides
DE2625764A1 (en) * 1976-06-09 1977-12-29 Bayer Ag TRIFLUOROMETHYLTHIO-PHENYL (DI) -THIO -PHOSPHORIC ACID ESTER, METHOD FOR THEIR PRODUCTION AND USE AS INSECTICIDE AND ACARICIDE
DE2709932A1 (en) * 1977-03-08 1978-09-14 Bayer Ag TRIFLUORMETHYLSULFINYLPHENYLTHIONO (THIOL) PHOSPHORIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES
DE2714038A1 (en) * 1977-03-30 1978-10-19 Bayer Ag TRIFLUORMETHYLSULFONYLPHENYLTHIONO (THIOL) PHOSPHORIC ACID ESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES
JPS55133389A (en) * 1979-04-03 1980-10-17 Takeda Chem Ind Ltd Organic phosphoric ester and insecticide comprising it

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH459657A (en) * 1964-07-10 1968-07-15 Bayer Ag Fungitoxic agent
US3839511A (en) * 1970-12-26 1974-10-01 Bayer Ag O-ethyl-s-n-propyl-o-(substituted phenyl)-phosphorothiolates

Also Published As

Publication number Publication date
FR2169223A1 (en) 1973-09-07
IL41306A (en) 1976-11-30
IT978469B (en) 1974-09-20
DE2303185A1 (en) 1973-08-09
HU167104B (en) 1975-08-28
BE794503A (en) 1973-07-25
ES410937A1 (en) 1976-05-16
GB1421561A (en) 1976-01-21
DD103142A5 (en) 1974-01-12
IL48344A0 (en) 1975-12-31
IL41306A0 (en) 1973-03-30
GB1421562A (en) 1976-01-21
JPS6036403B2 (en) 1985-08-20
NL7301018A (en) 1973-07-30
JPS4882042A (en) 1973-11-02
DE2303185C2 (en) 1986-01-09
FR2169223B1 (en) 1979-01-19
AT319662B (en) 1975-01-10

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