IE41530B1 - New phenyl carbamates - Google Patents
New phenyl carbamatesInfo
- Publication number
- IE41530B1 IE41530B1 IE2572/74A IE257274A IE41530B1 IE 41530 B1 IE41530 B1 IE 41530B1 IE 2572/74 A IE2572/74 A IE 2572/74A IE 257274 A IE257274 A IE 257274A IE 41530 B1 IE41530 B1 IE 41530B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound according
- parts
- cii
- compound
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
New phenyl carbamates of the formula (I) wherein R1 and R2 each represent hydrogen, C1-C4-alkyl, chlorine or bromine, R3 and R4 each represent methyl, or together they represent -CH2-CH2-,-CH2-CH2-CH2-, , , , , , , , or . are disclosed, processes for their production and their use in pest control.
Description
The present invention relates to phenyl carbamates, to processes for their production, and to their use in post control.
The phenyl carbamates concerned have the formula
(I) wherein R^ and R2
R^ and each represent hydrogen, C^-C^-alkyl, chlorine or bromine, each represent methyl, or together they represent
-ch2-ch2-, -ch2-ch2-ch2- , -CH-CH,1 2 CH3 , -CH—. θΗ3 -ch- , ch3 -C-CH,- , -CH-CH,-CH„- , -c- —c- , /\ 2 1 2 2 /\ z'\ CH3 CH3 ch3 ch3 ch3 ch3 ch . CH, 1 -CH-C- , I | -CH,-C-CH,- , V \ z -CH-CH-CH- or 1 I Ich3 CH3 CH3 ch3 CH3 ch3 ch3
-CH-CH,-CI 2/\ CII3 ch3 ch3
- 2 S'
Compounds of formula I preferred on account of their action are tiiosc wherein represents hydrogen,
R2 represents hydrogen, chlorine, methyl or tert.-butyl,
R3 and R4 together represent -CH2-CH2- , -CK-CH- ,-CH-CH2 ch3· ch3 in3 or-CH2-CH2-CH^-.
The compounds of formula I following methods known per se can be produced by the
T 3
Β 0
(III)
In the formulae II to IV, the symbols to R^ have the meanings given for formula I, and X stands for halogen, especially for chlorine, and Me stands for a metal, particularly an alkali metal.
Suitable acid-binding agents are: tertiary amines, e.g., trialkylamines, pyridine or dialkylanilines; inorganic bases such as hydrides or hydroxides; and carbonates and bicarbonates of alkali metals and alkaline-earth metals. It is sometimes necessary to use catalysts in the reactions, such as, e.g., copper or copper chloride.
The reactions A and B are performed under normal pressure at a temperature of between -20 and 50°C, preferably between .
0 and 30°C, and in solvents or diluents. These are, in particular, lower aliphatic ketones such as acetone or methyl
- 4 41530 ethyl ketone; alkanols such as methanol, ethanol or isopropanol; esters such as acetic acid ethyl ester; nitriles such as acetoniLrile; N-alkylated acid amides; aromatic and halogenated hydrocarbons, such as benzene, toluene, chloroform or methylene chloride; ethers and ethereal compounds, such as diethyl ether, dioxane or tetrahydrofuran; and also water and, in addition, mixtures of such solvents with each other and with water.
Starting materials of formulae II, III and IV are known and can be produced by methods analogous to known methods.
A process for the produel i on of the starting, products II and IV is described, for example, in the English Patent Specification No. 1,122,633.
The compounds of formula I have a broad biocidal action, and are therefore suitable for the control of various vegetable and animal pests. They possess however, above all, insecticidal and acaricidal properties, and can be used against all development stages, such as, e.g., eggs, larvae, pupae, nymphs and adults of insects and members of the order Acarina, such as, e.g., against insects of the families: Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduviidae, Phyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabacidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Lymatriidae, Pyralidae,
- 5 41530
Culcidae, Tripulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoridae and Pulicidae, as well as acarids of the families: Ixodidae, Argasidae, Tetranychidae and Dermanyssidae.
The compounds of formula I exhibit a particularly good action against insects of the families BIattidae and Chrysomelidae; especially, for instance, against Phyllodromia germanica, Periplaneta americana and Blatta orientalis or Leptinotarsa decemlineata.
The insecticidal or acaricidal action can be appreciable broadened and adapted to suit the given circumstances by the addition of other insecticides and/or acaricides. Suitable additives are, for example: organic phosphorus compounds, derivatives of nitrophenols, formamidines, ureas, carbamates, and/or chlorinated hydrocarbons .
The toxicity towards warm-blooded animals of compounds of formula I is surprisingly substantially lower than that of similar compounds known from the English Patent· Spec.
No. 1,122,633.
The compounds of formula 1 can he used on their own or together with suit able carriers and/or additive's. Suitable carriers and additives may be solid or liquid, and they correspond to the substances common in
I formulation practice, such as, for example, natural or regenerated .substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders and/or fertilisers .
For application, the compounds of formula Ϊ can be processed into the form of dusts, emulsion concentrates, granulates, dispersions, sprays or solutions, the formulation of these preparations being effected in a manner commonly known in practice.
The compositions according to tiie invention are prepared in a manner known per so by the intimate mixing and/or grinding of active substances of formula I with suitable carriers, optionally with the addition of dispersing agents or solvents which are inert to the active substances.
The active substances can be obtained and used in the following form;·;:
sol 1d pre para i ί »ns: - dusts, scattering agents, granulates, coated granulates, impregnated granulates and homogeneous granulates;
- 7 41530 liquid preparations:a) water-dispersible active-substance concentrates: wet table powders, pastes or emulsions;
b) solutions.
The content of active substance in the above described agents is between 0.1 and 95%; it is to be mentioned in this connection that in the case of application from an aeroplane, or by means of other suitable application devices, it is possible to employ also higher concentrations 10 The active substances of -formula I can he formulated, for example, as follows:
Dusts:
The following substances are used in the preparation of a) a 5% dust, and b) a 2% dust:
a) 5 parts of active substance, parts of talcum;
b) 2 parts of active substance, part of highly dispersed silicic acid, parts of talcum.
The active substances are mixed and ground with the carriers.
- 8 41530
Gramil ate:
The ί o.l 1 ow i ng, sub:.I ;uii <:; are us< d I» pi epnrc a 5% granulate:
part.:; of active substance,
0.25 part of epichlorohydrin,
0,25 pari, of cetyl polyglycol. ether,
3.50 parts of polyethyl erne glycol, parts of kaolin (particle size 0.3 - 0.8 mm). The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone; the polyethylene glycol and cetyl polyglyeol ether are then added. The solution thus obtained is sprayed onto kaolin, and the acetone is subsequently evaporated off in vacuo.
Wettable powder:
The following constituents arc used for the preparation
a)
b)
a 40%, b) and 40 parts of 5 parts of 1 part of 54 parts of 25 parts of 4.5 . parts of 1.9 parts of mixture I 1.5 parts of 19.5 parts of
- 9 41S30
19.5 parts of Champagne chalk,
28.1 parts of kaolin; ’ ' ’
c) 25 parts of active substance,
2.5 parts of isooctylphenoxy-polyoxyethylene-cthanol • 1.7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1),
8.3 parts of sodium aluminium silicate,
16.5 parts of· kicselguhr, parts of kaolin;
d) 10 parts of active substance, '3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphates, parts of naphthalenesulphonic acid/formaldehyde condensate, parts of kaolin.
The active substances are intimately mixed, in suitable mixers, with the additives, and the mixture is then ground in t-he appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to give suspensions of any desired concentration.
Emulsifiable concentrates : '
The following substances are used to prepare a) a 10% and b) a 25% emulsifiable concentrate:
a) 10 parts of active substance,
3.4 parts of epoxidised vegetable oil,
--10-. - .
3.4 parts of a combination emulsifier consisting of fatty alcohol, polyglycol ether and alkylaryl sulphonate calcium salL, 40 parts of diiiieLhylformaniide, 5 43.2 parts of xylene; b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil., 10 parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture, 10 5 parts of dimethylformamide, 57.5 parts of xylene.
From those concentrates it j.s possible to prepare, by dilution with water, emulsions of any desired concentration.
Spray:
The following constituents are used to prepare a 5% spray:
parts of active substance, part of e.pichlor hydrin, parts of ligroin (boiling limits ICO - 190°C).
Exampl e 1
Production of N-methyl-N-p-chloromercapto-phenyl-O-(1,3di oxan-2-yl) -phenyl carbamate g of p-chlorophenylsulphenyl chloride is added dropwise at 5 - 10°C, with continuous stirring, to a mixture of
23.7 g of N-methyl-0-(l,3-dioxan-2-yl)-phenyl-carbamate and 50 ml of pyridine. After the reaction mixture has been stirred for 30 minutes at room temperature, it is poured into a solution of 150 ml of ice-water and 40 ml of concentrated hydrochloric acid, and the whole is stirred for a further 30 minutes. The reaction product is extracted with methylene chloride, the extract is washed with water, dried over sodium sulphate and concentrated by evaporation.
After reerystallisation of the solid residue from methanol, there is obtained the compound of the formula
CH
0/ \)
I I oh2 /Ch2
CH„ in the form of white crystalline powder having a melting point of 108.6 - 109.8°G.
The following further compounds of formula I are produced in an analogous manner:
;Ri ' R2R3R4 Physical data p-Cl H -CH2 -ch2- M.P. 132,5- 134°C p-Cl H -CH- -CH- 20° n^ = 1,5927 ch3 ch3 H H -ch2- -CH - M.P. 85 - 87°C H H -ch2-CR2~Cn2”2θ° 1 ηβ - 1,5820 H H -CH- -CH- ?n° η» = 1,5691 θΗ3 ra3 H H CH3CIi3 20 ηθ - 1,5703 p-CII3 H CH3 C1I3 20 Πρ = 1,5672 p-CIl3 H -CH2- C1I2- M.P. 73,2 - 75,6°C 2-Cl 5-Cl -ch2- cn2- M.P. 65 - 67°C pcii3 II -CH— CII- n^° = 1,5649 CH3 CH3 2 -Cl 5-C1 -CH— CII-n3° = 1,5791 ch3 cn3 p-Cl H -c- -CH- M.P. 49 - 52°C C1I3 ch3 CH3 II H >GC CH3 CH —CH- 3 n|° = 1,5567 11 II -CII, CII9χ / 2 M.P. 80 - 82°C
CH3 CII3
*1 r2 R3R4 Physical data • p-Cl H -CH„ CH„ - M.P. 113 - 114°C \/ vp CH3 cn3 p-Cl H -CH—CH—CH- M.P. 97 - 103°C ch3 cii3 ch3 p-CH3 II -CH—CH—CH- n^° = 1,5542 ch3 ch3 ch3 H H -ch-ch„-ch2 n^° = 1,5677 ch3 2-Cl *-Cl ch3 ch3 M.P. 80 - 82°C m-CII3 H -ch2· -CH2- 20 = 1,5818 o-CH3 H -CH- -CH- 20 = 1,5681 CH3CH3 p-CH3 H -CH2-CH2-CH2- n^° = 1,5756 o-CH3 H -CH2-CH2-CH2- M.P. 107 - 1O8°C 2-Cl •5-Cl -CH2-CH2-CII2- M.P. 1.15 -117°C p-Br H -ch2- CH2- M.P. 136 - 140°C p-Br H -CH— CH- ch3 ch3 p-Br H -c-ch2-ch- * (ch3)2 cii3
- 14 41530
R1R2R3 R4 Physical data • p-cl H -C-C1I2-CH- (CII3)2 CH3 o-CH3 H -CH2-CH2- M.P. 77 - 79°C o-CH3 II -C·-CIl- 20 ηθυ = 1,5600 (CII3)2 ch3 p-Cl II -C--c- M.P. 80 - 82°C (CI13)2(C1I3)2 H H 1 -CH3-C1I-CII3 n20 = 1,5769 p-Cl H -CH2-fclI-CII3 p-ch3 H -CH2-CH-C1I3 n20 = 1,5721 2-Cl 5-Cl -CH2-tn-CH3 2-Cl 5.-C1 CH3-0lI-0 M.P. 80 - 83°C (ch3)2 Pi-C4H9 H -ch2-ch2- 20 rip = 1,5644 Pi‘C4H9 H -ch2-ch2-ch2- M.P.77 - 80°C
Example 2 ]n order Lo Lest lhe action of I he compounds against various pests of the families Blattidae and Chrysomelidae, an amount in each case of 2 g of the compounds according to
Example 1 was mixed with 38 g of talcum, and the whole was ground as fine as possible. The result was a very effective dusting powder, with which the areas infested by the pests were treated. Dusting powders containing any one of the compounds according to Example 1 exhibited a good action lo against Phyllodromia germanica, Periplaneta americana and
Blatta orientalis or Leptinotarsa decemlineata.
- 16 41530
Example 3
Insecticidal stomach poison action
Cotton and potato plants were sprayed with a 0.05% aqueous active-substance emulsion (obtained from a 10% emulsifiable concentrate).
After the drying of the resulting coating, Spodoptera 11ttoralis or Heliothis vlrescens larvae were placed onto the cotton plants, and Colorado beetle larvae (Leptinotarsa decemlineata) onto the potato plants. The lo test was carried out at 24°C with 60% relative humidity.
The compounds according to Example 1. exhibit c.d in the above test a good insecticidal stomach poison action against Spodoptera lit 1 oralis, Heliothis vlrescens and Leptinotarsa decemlineata larvae.
Example h
Action again;:!· Chilo suppressalis
Rice plants of the type Caloro were planted, 6 plants per pot, in plastic pots having a top diameter of 17 cm, and grown to a height of about 60 cm. Infestation with
Chilo suppressalis larvae (L^; 3-4 mm long) was carried out 2 days after application of the active substance in granular form (amount applied = 8 kg of active substance per hectare) to the paddy water. The evaluation of the 0 insecticidal action was made 10 days after application of the granules .
The compounds according to Example 1 were effective against Chilo suppressalis in the above test.
- 18 41530
Example 5
Action against- soil Insects
Sterilised compost soil is homogeneously mixed with a wettable powder containing 25% of active substance; the amounts are so adjusted that a concentration range of
16, 8, 4, 2 and 1 ppm is obtained. Young zucchetti plants and young cabbage plants are placed into the thus treated soil; the soil is immediately infested with 5 larvae of Aulacophora femoralis (age : 15 d/25°C) in the one case, and with 15 eggs of Chortophila brassicae (cabbage root-fly) in the other case; a third corresponding soil series is provided with slices of apple as feed and 5 larvae of Paehnoda savignyi (20 d/25°C) are put into the soil.. An assessment of mortality is made 10 days after application and infestation. The screening test with cutworms (Agrotis Y-I^) is performed analogously, with the exception that the concentration series is 40, 20 and 10 ppm.
Mallow leaves are used as feed.
The compounds according to Example 1 were effective against Aulacophora femoralis larvae, Chortophila brassicae larvae, Paehnoda savignyi larvae and Agrotis laryae in the above tests.
Example 6
Comparison of toxicity towards warm-blooded animals
The toxicity towards warm-blooded animals in the case of the following compound according to the invention is substantially lower than that of the compound known from
I, the English Patent Specification No. 1,122,633, as is shown by the following results.
(DL 50 rat p.o. acute):
ch2—ch2
according to the invention 1100 mg/kg known from the
English Patent Specification No. 1,122,633 60 mg/kg
Claims (4)
1. Phenyl carbamates of the formula wherein R^ and R 2 R^ and R^ 41630 each represent hydrogen, C^-C^-alkyl, chlorine or bromine, each represent methyl, or together they represent -CH 2 -CH 2 -,“CH 2 -CH 2 -CH 2 - , -CH-CH 2 ch 3 -C-CH, /\ 2 CH 3 ch 3 ? H 3 -ch—οΙ I CH 3 CH 3 -ch 2 -c^h 2 ch 3 ch 3 CHI CH, J CHI CH 3 -CH-CH 0 -CII 0 - , -C-C- ) I 2 2 /\ /\ CH 3 CH 3 ch 3 CH 3 CH 3 •CH-CH-CHI ! I CH 3 CH 3 ch 3 or -CH-CH,-CI 2 /\ CH 3 ch 3 CH 3 - 21 41530 or or 3. 3. Compounds of formula (I) according to Claim 1, wherein represents hydrogen, represents hydrogen, chlorine, methyl or tert.-butyl, I R 4 together represent -CH 2 -CH 2 -, -CH—CII- , -CH—CH 2 ~ ch 3 ch 3 ch 3 -ch 2 -cii 2 -ch 2 -. Compound according to Claim 2 of the formula CH^—CH 2 Compound according to Claim 2 of the formula 0 CH. 22 41530 formula 6. Compound according to Claim 2 of the formula CH (/ \) CH 2 —cii 2 7. Compound according to Claim 2 of the formula CH (/ x 0 CHx—CH ' CH23 Compound according to Claim 2 of the formula CH d \) i I CHg—CH CEL 9. 5 10. Compound according to Claim 2 of the formula CH 0 / \i I · I •0H,T— CH 2 I CH q Compound according to Claim 1 of the formula 0 / \) I I CHr—CH 2 I CH 3 - 24 41530 11. Compound according to Claim 2 of the formula CH-CH I I CH, CH, J J 12. Compound according to Claim 1 of the formula 5 13 Compound according to Claim 1 of the formula CH (/ \) . CH 3 CH 3 CII 3 I 14. Compound according to Claim 2 of the formula CH (/ X 0 I I ch 2 ^C1I 2 15. Compound according to Claim 1 of the formula Cl CH,- C-C—CH, 3 I | 3 CH CH
2. 5 16. Compound according to Claim 1 of the formula 3 ’ i CH„ CH, - 26 41530 17. Process for the production of a compound according to Claims 1 to 16, wherein a compound of the formula is reacted with a compound of the formula in the presence of an acid-binding agent, or with a compound of the formula wherein R^ to R^ have the meanings given in Claim 1, and 10 X stands for halogen, and Me stands for a metal. 18. Pest-control compositions containing as the active constituent a compound according to Claims 1 to 16, together with suitable carriers and/or other additives. 19. Use of compounds according to Claims 1 to 16 for the control of vari ous animal and plant pests . 20. Use according to Claim 19 for the control of insects 5 and members of the order Acarina. 21. Use according to Claim 20' for the control of insects of the families Blattidae and Chrysomelidae. 22. Process for the preparation of phenyl carbamates of the formula (i) given and defined in claim 1 substantially
3. 10 as hereinbefore described with reference to example 1. 23· Phenyl carbamates of the formula I given and defined in claim 1 whenever prepared by a process claimed in a preceding claim. 24. Pest-control compositions substantially as hereinbefore
4. 15 described.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1745173A CH586508A5 (en) | 1973-12-14 | 1973-12-14 | 2-Formylphenyl-N-methyl-N-phenylthio-carbamate acetals - with insecticidal and acaricidal activity |
| CH1524574 | 1974-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41530L IE41530L (en) | 1975-06-14 |
| IE41530B1 true IE41530B1 (en) | 1980-01-30 |
Family
ID=25715977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2572/74A IE41530B1 (en) | 1973-12-14 | 1974-12-13 | New phenyl carbamates |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5094131A (en) |
| AT (1) | AT335798B (en) |
| AU (1) | AU7638774A (en) |
| CA (1) | CA1042448A (en) |
| DE (1) | DE2458689A1 (en) |
| DK (1) | DK614474A (en) |
| ES (1) | ES432875A1 (en) |
| FR (1) | FR2254563B1 (en) |
| GB (1) | GB1486456A (en) |
| IE (1) | IE41530B1 (en) |
| IL (1) | IL46199A (en) |
| IT (1) | IT1049337B (en) |
| LU (1) | LU71468A1 (en) |
| NL (1) | NL7416143A (en) |
| SE (1) | SE7414929L (en) |
-
1974
- 1974-11-26 DK DK614474A patent/DK614474A/da unknown
- 1974-11-28 SE SE7414929A patent/SE7414929L/en not_active Application Discontinuation
- 1974-12-06 IL IL46199A patent/IL46199A/en unknown
- 1974-12-11 NL NL7416143A patent/NL7416143A/en not_active Application Discontinuation
- 1974-12-11 FR FR7440784A patent/FR2254563B1/fr not_active Expired
- 1974-12-11 DE DE19742458689 patent/DE2458689A1/en not_active Withdrawn
- 1974-12-12 CA CA215,912A patent/CA1042448A/en not_active Expired
- 1974-12-12 LU LU71468A patent/LU71468A1/xx unknown
- 1974-12-13 ES ES432875A patent/ES432875A1/en not_active Expired
- 1974-12-13 IT IT30554/74A patent/IT1049337B/en active
- 1974-12-13 AT AT997474A patent/AT335798B/en not_active IP Right Cessation
- 1974-12-13 IE IE2572/74A patent/IE41530B1/en unknown
- 1974-12-13 JP JP49144009A patent/JPS5094131A/ja active Pending
- 1974-12-13 AU AU76387/74A patent/AU7638774A/en not_active Expired
- 1974-12-13 GB GB54058/74A patent/GB1486456A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7416143A (en) | 1975-06-17 |
| CA1042448A (en) | 1978-11-14 |
| LU71468A1 (en) | 1975-08-20 |
| DE2458689A1 (en) | 1975-06-19 |
| IL46199A0 (en) | 1975-03-13 |
| GB1486456A (en) | 1977-09-21 |
| FR2254563B1 (en) | 1978-02-24 |
| ES432875A1 (en) | 1977-02-16 |
| DK614474A (en) | 1975-08-11 |
| SE7414929L (en) | 1975-06-16 |
| IE41530L (en) | 1975-06-14 |
| ATA997474A (en) | 1976-07-15 |
| IT1049337B (en) | 1981-01-20 |
| IL46199A (en) | 1977-05-31 |
| AU7638774A (en) | 1976-06-17 |
| FR2254563A1 (en) | 1975-07-11 |
| AT335798B (en) | 1977-03-25 |
| JPS5094131A (en) | 1975-07-26 |
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| DE2430758A1 (en) | Oxadiazolyls from hydroxydiazoles and phosphoric acid halides - with wide biocidal activity | |
| CH564909A5 (en) | 1-Phosphoryl-5-amino-1,2,4-triazoles - as insecticides and acaricides from 5-aminotriazoles and bis-dimethylaminophosphoryl-chloride |