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GB1579635A - Sulphenamides and their use in pesticidal compositions - Google Patents

Sulphenamides and their use in pesticidal compositions Download PDF

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Publication number
GB1579635A
GB1579635A GB25871/77A GB2587177A GB1579635A GB 1579635 A GB1579635 A GB 1579635A GB 25871/77 A GB25871/77 A GB 25871/77A GB 2587177 A GB2587177 A GB 2587177A GB 1579635 A GB1579635 A GB 1579635A
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compound
formula
test
plants
parts
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GB25871/77A
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Novartis AG
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Ciba Geigy AG
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Priority claimed from CH767936A external-priority patent/CH608692A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1579635A publication Critical patent/GB1579635A/en
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    • 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
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (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)

Description

(54) SULPHENAMIDES AND THEIR USE IN PESTICIDAL COMPOSITIONS (71) We, CIBA-GEIGY AG, a Swiss body corporate, of Basle, Switzerland, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to novel N,N'-bis-carbamic acid sulphide derivatives which act against pests, to a process for their manufacture and to pesticidal compositions which contain these derivatives as active ingredient, and to a method of controlling pests which comprises the use of the novel compounds.
The N,N'-bis-carbamic acid sulphide derivatives according to the invention have the formula I
wherein R1 represents a methyl or ethyl group, R2 represents a C1Cs-alkyl or C3Cs-cycloalkyl group and R, represents a hydrogen atom or a C1JC,-alkoxy or cyclopropyl group, with the proviso that, when R1 and R2 both represent methyl groups, R, is not a methoxy, ethoxy, n-butoxy or t-butoxy group.
Alkyl groups R2 can be branched or straight chain. Possible groups subject to the proviso are for example the methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl and tert.-butyl group as well as the n-pentyl, n-hexyl and n-octyl group and the isomers thereof. Such groups, up to and including hexyl, also form the alkyl moiety of alkoxy groups represented by R,. By C3~Cs-cycloalkyl groups are meant for example cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups.
Particularly preferred compounds on account of their action against pests, especially against insects, are those of the formula I wherein R2 represents a C1-C4-alkyl, cyclopropyl, cyclohexyl or cyclooctyl group, and R, represents a hydrogen atom or a C1C4-alkoxy or cyclopropyl group.
The compounds of the formula I may be obtained by methods which are known per se, for example by reacting a compound of the formula II
wherein R1 is as defined in formula (I), in the presence of a base, with a compound of the formula III
wherein R2 and R, are as defined in formula I and Hal represents a halogen atom, in particular a chlorine or bromine atom.
The process is generally out at a reaction temperature between 200 and + 800C, at normal or elevated pressure and preferably in a solvent or diluent which is inert to the reactants. Suitable solvents or diluents for the reaction are for example: ethers and ethereal compounds, such as diethyl ether, diisopropyl ether, dioxan, dimethoxyethane and tetrahydrofurane; amides, such as N,N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, methylene chloride, chloroform and chlorobenzene; nitriles, such as acetonitrile; dimethyl sulphoxide; and kenotes, such as acetone and methyl ethyl ketone.
Suitable bases are tertiary amines, such as triethylamine, dimethyl aniline, pyridine, picolines and lutidines, and hydroxides, oxides, carbonates and bicarbonates of alkali metals and alkaline earth metals as well as alkali metal alcoholates, for example potassium tert.butylate and sodium methylate.
The compounds of the formulae II and III used as starting materials are known (see for example US patent specification 3,506,698) or they can be prepared in accordance with known methods.
The compounds of the formula I have a broad biocidal action and can be used for controlling a variety of pests, for example as insecticides, acaricides, ectoparasiticides, nematicides and fungicides.
The compounds of the formula I are suitable chiefly for controlling insects. They can thus be used for example for controlling insects of the families Lymantriidae, Noctuidae, Pyralidae, Tineidae, Bruchidae, Chrysomelidae, Curculionidae, Dermestidae, Scarabaedae, Tenebrionidae, Aphididae, Diaspididae, Cimicidae, Pyrrhocoridae, Reduviidea, Agromycidae, Anthomyiidae, Calliphoridae, Culicidae, Muscidae, Stomoxidate, Tipulidae, Trypetidae, Acrididae, Blattidae, Gryllidae and Gryllotalpidae.
The compounds of the formula I are suitable in particular for controlling insects which are injurious to plants (e.g. insects of the genus Spodoptera, Dysdercus, Heliothis, Aphis, Pseudococcus and Chilo) in crops of useful plants and in ornamentals, in particular in crops of rice, cotton, fruit and vegetables.
The insecticidal or acaricidal action can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticides and/or acaricides.
Examples of suitable additives are: organic phosphorus compounds, nitrophenols and derivatives thereof, formamidines, ureas, pyethroids, carbamates, and chlorinated hydrocarbons.
The compounds of the formula I may be used as pure active substance in composition form together with (i) a solid extender, or (ii) a liquid diluent and a surface active agent.
Suitable additives can be solid or liquid and correspond to the substances conventionally used in the art of formulation, for example natural or regenerated substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders and/or fertilisers.
For application, the compounds of the formula I may be processed to dusts, emulsifiable concentrates, granules, dispersions, sprays, solutions, or suspensions, in the conventional formulation which is commonly employed in application technology.
The compositions of the present invention may be manufactured in known manner e.g. by homogeneously mixing and/or grinding active substances of the formula I with the suitable extenders, with or without the addition of dispersants or solvents which are inert to the active substances.
The compounds of the formula I may be processed to the following formulations: Solid formulations: Dusts, tracking agents and granules (coated granules, impregnated granules and homogeneous granules).
Liquid formulations: a) active substances which are dispersable in water: wettable powders, pastes and emulsions; b) solutions.
The content of active substance in the above described compositions is generally between 0.1% and 95%, though higher concentrations can also be used if the compositions are applied from an aircraft or other appropriate application devices.
The compounds (active substances) of the formula I can, for example, be formulated as follows (throughout the present specification all parts and percentages are by weight): Dusts The following substances are used to manufacture a) a 5% and b) a 2% dust: a) 5 parts of active substance, 95 parts of talc; b) 2 parts of active substance, 1 part of highly disperse silicic acid, 97 parts of talc.
The active substances are mixed with the extenders 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, 3.50 parts of polyethylene glycol, 91 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 polyglycol ether are then added. The resultant solution is sprayed on kaolin, and the acetone is subsequently evaporated in vacuo.
Wettable powder: The following constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d) a 10 %wettable powder: a) 40 parts of active substance, 5 parts of sodium lignin sulphonate, 1 part of sodium dibutylnaphthalenesulphonate, 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 mixture (1:1), 1.5 parts of sodium dibutylnaphthalenesulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalk, 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 sodium salts of saturated fatty alcohol sulphates, 5 parts of naphthalenesulphonic acid/formaldehyde condensate, 82 parts of kaolin.
The active substances are homogeneously mixed with the additives in suitable mixers and the mixture is then ground in appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to give suspensions of the desired concentration.
Emulsifiable concentrates: The following substances are used to produce a) a 10%, b) a 25%, and c) a 50% emulsifiable concentrate: a) 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, 3.4 parts of a combination emulsifier consisting of fatty alcohol polyglycol ether and alkylarylsulphonate calcium salt, 40 parts dimethyl formamide, 43.2 parts of xylene; b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, 10 parts of alkylarylsulphonate/fatty alcohol polyglycol ether mixture, 5 parts of dimethyl formamide, 57.5 parts of xylene; c) 50 parts of active substance, 4.2 parts of tributylphenol-polyglycol ether, 5.8 parts of calcium dodecylbenzenesulphonate, 20 parts of cyclohexanone, 20 parts of xylene.
By diluting these concentrates with water it is possible to obtain emulsions of the required concentration.
Spray: The following ingredients are used to prepare a) a 5% spray, and b) a 95% spray: a) 5 parts of active substance, 1 part of epichlorohydrin, 94 parts of ligroin (boiling range 1600--190"C); b) 95 parts of active substance, 5 parts of epichlorohydrin.
The invention is further illustrated by the following Examples.
Example 1.
Preparation of N - (N - methylcarbamic acid - 1 - methylthioethylimide - N' - (N' methylcarbamic acid - n - hexyl ester) - sulphide With stirring, 15.8 g of N - chlorosulphenyl - N - methyl - n - hexylurethane and then 6.6 g of pyridine were added dropwise at 50 to 100C to a solution of 11.3 g of 1 - methyl - thioethylidenamino - N - methylcarbamate in 70 ml of dichloromethane.
The reaction mixture was then stirred for 16 hours at a temperature of 5 to 100C.
The pyridine hydrochloride which had formed was subsequently filtered off by suction, the dichloromethane distilled off, and the crude product chromatographed over silica gel (benzene/methyl acetate), giving the N - (N - methylcarbamic acid - 1 - methylthioethylimide) - N' - (N' - methylcarbamic acid - n - hexyl ester) - sulphide of the formula
(Compound 1) with a melting point of 45"C.
The following compounds of the formula I can be obtained in analogous manner:
Physical Compound Rl R2 R3 data 2 CH,- CH3- f m.p. 55-590C ~ ~ , ~. 3 CH3- 9 H n2D0 1.5529 4 CH3- (n)C4H9- n)C4H9O- m.p. 62-66"C 5 2Hs- CH3- n)C6H,30- 22 1.5100 nD: 6 CH3- CH3- H nj:1.5450 20 7 C2H5- CH3- H oD: 1.5407 8 CH3- (n)C4H9 CH3O- m:P. 900C 9 C2Hs- (n)C4H9 CH3O- n2D :1 1.5099 10 CZH,- CH3- m.p. 104-106"C 11 CH3- cyclooctyl H "20 1.5534 nD: 12 C,H,- cyclooctyl H 20 : 1.5483 13 CH,- k H m.p. 54-580C 14 C,H,- H nj2D0 1.5468 20 15 C2Hs CH3 (n)C4H9O- n2D0 1.5158 16 CH, C2HsCH CH H 15218 - H nD: (n)C4H9 17 C,H, > CH-CH2- H n2DO: 1.5183 (n)C4H9
Example 2.
Insecticidal stomach poison action: Spodoptera littoralis, Dysdercus fasciatus and Heliothis virescens Cotton plants were sprayed with an aqueous emulsion containing 0.05% of the compound to be tested (obtained from a 10% emulsifiable concentrate).
After the spray coating had dried, the plants were populated with larvae (L3.stage) of the species Spodoptera littoral is, Dydercus fasciatus or Heliothis virescens. Two plants were used for each test compound and test species. Evaluation of mortality was made after 2, 4, 24 and 48 hours. The test was carried out at 240C and 60% relative humidity.
In this test, the compounds of Example 1 exhibited a very good action against larvae of the species Spodoptera lottoralis, Dysdercus fasciatus and Heliothis virescens.
Example 3.
Insecticidal contact action: Aphis fabae Plants (Vicia faba) which have been reared in pots were each populated before the start of the test with approx. 200 aphids of the species Aphis fabae. The treated plants were sprayed dripping wet 24 hours later with a solution containing 1000 or 100 ppm of the compound to be tested. Two plants were used for each test compound and test concentration. Evaluation of mortality was made 24 hours later.
In this test, the compounds of Example 1 exhibited a positive action against Aphis fabea.
Example 4.
Insecticidal contact action: Pseudococcus citri Plants (Vicia faba) which have been reared in pots and cut back to a welldeveloped pair of leaves, were populated with approx. 200 lice of the species Pseudococcus citri 24 hours before the start of the test. The undersides of the leaves populated with lice were then sprayed dripping wet next day with a test solution containing 500 ppm of the compound to be tested. Two plants were used for each test substance and evaluation of mortality was made 24 and 48 hours respectively after the start of the test.
In this test, the compounds of Example 1 acted against Pseudococcus citri.
Example 5.
Insecticidal action: Chilo suppressalis Rice seedlings of the variety Caloro were reared in plastic pots (6 seedlings per pot) so that their roots became matted to a disc. The roots were then immersed in a solution containing 800, 200 or 100 ppm of the active compound to be tested and allowed to drip off. Then each pot was populated with 5 Chilo suppressalis larvae in the L2-stage and the treated plants were subsequently replaced in the pots on top of the larvae.
One plant was used for each test substance and concentration, and evaluation of mortality (in ! ) was made after 5 days. The test was carried out at 240C and 70% relative humidity.
In this test, the compounds of Example 1 exhibited a good action against Chilo suppressalis.
WHAT WE CLAIM IS: 1. A compound of the formula I
wherein R, represents a methyl or ethyl group, R, represents a C1C8-alkyl or C,--C,-cycloalkyl group and R, represents a hydrogen atom or a ClCG-alkoxy or cyclopropyl group, with the proviso that, when Rl and R2 both represent methyl groups, R3 is not a methoxy, ethoxy, n-butoxy or t-butoxy group.
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (37)

**WARNING** start of CLMS field may overlap end of DESC **. Example 2. Insecticidal stomach poison action: Spodoptera littoralis, Dysdercus fasciatus and Heliothis virescens Cotton plants were sprayed with an aqueous emulsion containing 0.05% of the compound to be tested (obtained from a 10% emulsifiable concentrate). After the spray coating had dried, the plants were populated with larvae (L3.stage) of the species Spodoptera littoral is, Dydercus fasciatus or Heliothis virescens. Two plants were used for each test compound and test species. Evaluation of mortality was made after 2, 4, 24 and 48 hours. The test was carried out at 240C and 60% relative humidity. In this test, the compounds of Example 1 exhibited a very good action against larvae of the species Spodoptera lottoralis, Dysdercus fasciatus and Heliothis virescens. Example 3. Insecticidal contact action: Aphis fabae Plants (Vicia faba) which have been reared in pots were each populated before the start of the test with approx. 200 aphids of the species Aphis fabae. The treated plants were sprayed dripping wet 24 hours later with a solution containing 1000 or 100 ppm of the compound to be tested. Two plants were used for each test compound and test concentration. Evaluation of mortality was made 24 hours later. In this test, the compounds of Example 1 exhibited a positive action against Aphis fabea. Example 4. Insecticidal contact action: Pseudococcus citri Plants (Vicia faba) which have been reared in pots and cut back to a welldeveloped pair of leaves, were populated with approx. 200 lice of the species Pseudococcus citri 24 hours before the start of the test. The undersides of the leaves populated with lice were then sprayed dripping wet next day with a test solution containing 500 ppm of the compound to be tested. Two plants were used for each test substance and evaluation of mortality was made 24 and 48 hours respectively after the start of the test. In this test, the compounds of Example 1 acted against Pseudococcus citri. Example 5. Insecticidal action: Chilo suppressalis Rice seedlings of the variety Caloro were reared in plastic pots (6 seedlings per pot) so that their roots became matted to a disc. The roots were then immersed in a solution containing 800, 200 or 100 ppm of the active compound to be tested and allowed to drip off. Then each pot was populated with 5 Chilo suppressalis larvae in the L2-stage and the treated plants were subsequently replaced in the pots on top of the larvae. One plant was used for each test substance and concentration, and evaluation of mortality (in ! ) was made after 5 days. The test was carried out at 240C and 70% relative humidity. In this test, the compounds of Example 1 exhibited a good action against Chilo suppressalis. WHAT WE CLAIM IS:
1. A compound of the formula I
wherein R, represents a methyl or ethyl group, R, represents a C1C8-alkyl or C,--C,-cycloalkyl group and R, represents a hydrogen atom or a ClCG-alkoxy or cyclopropyl group, with the proviso that, when Rl and R2 both represent methyl groups, R3 is not a methoxy, ethoxy, n-butoxy or t-butoxy group.
2. A compound as claimed in claim 1 wherein
R2 represents a C1-C4-alkyl, cyclopropyl, cyclohexyl or cyclooctyl group and R3 represents a hydrogen atom or a C1-C4-alkoxy or cyclopropyl group.
3. A compound as claimed in claim 1 wherein R2 represents a C1-C6-alkyl or C3-C6-cycloalkyl group.
4. A compound as claimed in claim 3 wherein R2 represents a ClC4-alkyl, cyclopropyl or cyclohexyl group.
5. The compound of the formula
6. The compound of the formula
7. The compound of the formula
8. The compound of the formula
9. The compound of the formula
10. The compound of the formula
11. The compound of the formula
12. The compound of the formula
13. The compound of the formula
14. The compound of the formula
15. The compound of the formula
16. The compound of the formula
17. The compound of the formula
18. The compound of the formula
19. The compound of the formula
20. The compound of the formula
21. The compound of the formula
22. Process for the production of a compound of the formula I as claimed in claim 1, which process comprises reacting a compound of the formula II
wherein Rl has the meaning given in claim 1 with a compound of the formula III
wherein R2 and R3 have the meanings given in claim 1 and Hal represents a halogen atom, said reaction being carried out in the presence of a base.
23. Process as claimed in claim 22 wherein in the compound of the formula II and consequently in the product of the formula I, R2 represents a C--C,-alkyl or Cs--C,- cycloalkyl group.
24. A pesticidal composition comprising a compound as claimed in any one of claims 1, 2 and 10 to 21 together with (i) a solid extender or (ii) a liquid diluent and a surface active agent.
25. A composition as claimed in claim 24 in the form of a wettable powder, paste, emulsion, emulsifiable concentrate or granulate.
26. A pesticidal composition comprising a compound as claimed in any of claims 3 to 9 together with (i) a solid extender or (ii) a liquid diluent and a surface active agent.
27. A composition as claimed in claim 26 in the form of a wettable powder, paste, emulsion, emulsifiable concentrate or granulate.
28. A method of controlling pests at a locus, which method comprises applying to said locus a compound as claimed in any one of claims 1, 2 and 10 to 21.
29. A method as claimed in claim 28 wherein the pests are insects.
30. A method as claimed in claim 28 or 29 wherein the locus comprises an agricultural or horticultural crop.
31. A method as claimed in claim 30 wherein the crop is a rice, cotton, fruit or vegetable crop.
32. A method of controlling pests at a locus, which method comprises applying to said locus a compound as claimed in any one of claims 3 to 9.
33. A method as claimed in claim 32 wherein the pests are insects.
34. A method as claimed in claim 32 or 33 wherein the locus comprises an agricultural or horticultural crop.
35. A method as claimed in claim 34 wherein the crop is a rice, cotton, fruit or vegetable crop.
36. Process for the production of a compound of the formula I as claimed in claim 1 substantially as described with reference to Example 1.
37. A compound of the formula I as claimed in claim 1 produced by the process claimed in claim 22, 23 or 36.
GB25871/77A 1976-06-22 1977-06-21 Sulphenamides and their use in pesticidal compositions Expired GB1579635A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH767936A CH608692A5 (en) 1976-06-22 1976-06-22 Pesticide comprising an N,N'-dicarbamic acid sulphide derivative as active ingredient
CH601577 1977-05-13

Publications (1)

Publication Number Publication Date
GB1579635A true GB1579635A (en) 1980-11-19

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ID=25698832

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GB25871/77A Expired GB1579635A (en) 1976-06-22 1977-06-21 Sulphenamides and their use in pesticidal compositions

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AT (1) AT353051B (en)
AU (1) AU512647B2 (en)
BR (1) BR7704031A (en)
CA (1) CA1080738A (en)
DE (1) DE2727614A1 (en)
EG (1) EG12927A (en)
FR (1) FR2355818A1 (en)
GB (1) GB1579635A (en)
IL (1) IL52362A (en)
IT (1) IT1082108B (en)
MX (1) MX4690E (en)
NL (1) NL7706779A (en)
SU (1) SU659064A3 (en)
TR (1) TR19827A (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2737606A1 (en) * 1977-08-20 1979-03-01 Bayer Ag ARYL-N-ALKYL-CARBAMATE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES
DE2828133A1 (en) * 1978-06-27 1980-01-10 Bayer Ag N-SULFENYLATED CARBAMOYLOXIMINO-1-METHYLTHIO-BUTANES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES
EP0049684B1 (en) * 1980-10-02 1985-08-07 Ciba-Geigy Ag N-(benzamidosulfenyl)-n-methyl carbamates, intermediates, preparation, and pesticidal use
JPS5892655A (en) * 1981-11-27 1983-06-02 Otsuka Chem Co Ltd Carbamate derivative, its preparation and insecticide containing said derivative as active component

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DE2530439C2 (en) * 1974-07-11 1983-03-03 CIBA-GEIGY AG, 4002 Basel Bis- [0- (1-alkylthio-ethylimino) -N-methyl-carbamic acid] -N, N'-sulfides, processes for their preparation and pesticides containing these compounds

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IT1082108B (en) 1985-05-21
AU512647B2 (en) 1980-10-23
TR19827A (en) 1980-01-24
ATA436077A (en) 1979-03-15
MX4690E (en) 1982-08-02
FR2355818B1 (en) 1980-03-14
AU2628477A (en) 1979-01-04
IL52362A (en) 1980-12-31
EG12927A (en) 1980-10-31
AT353051B (en) 1979-10-25
IL52362A0 (en) 1977-08-31
CA1080738A (en) 1980-07-01
SU659064A3 (en) 1979-04-25
BR7704031A (en) 1978-06-06
NL7706779A (en) 1977-12-27
FR2355818A1 (en) 1978-01-20
DE2727614A1 (en) 1978-01-05

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