CH596757A5 - N,N'-thiobis(O-(1-alkylthioethylimino)-N-methyl-carbamates) - Google Patents

Abstract

N,N'-thiobis(O-(1-alkylthioethylimino)-N-methyl-carbamates) with insecticidal and nematocidal activity

Description

  

  
 



   The present invention relates to a pest control agent containing as active component a bis (O- (1-alkylthio-ethylimino) -N-methylcarbamic acid) -N, N'-sulfide and its use for pest control.



   The bis (0- (1 alkylthio-ethylimino) -N-methylcarbamic acid) -N, N'-sulfides contained in the agent according to the invention are those of the formula I.
EMI1.1
 wherein R is a C1-Cs-alkyl group.



   The alkyl groups in question for R can be branched or straight-chain. Examples of such groups are: methyl, ethyl, propyl, isopropyl, n-, i-, sec-, tert-butyl and n-pentyl.



   The compounds of the formula I in which R is a methyl or ethyl group are preferred because of their action.



   The compounds of the formula I can be prepared by the following methods known per se:
EMI1.2


<tb> <SEP> a) RS-C <SEP> = <SEP> WOC-NR + S2CL <SEP> Base <SEP> '<SEP> (I)
<tb> <SEP> I <SEP> II <SEP> I
<tb> <SEP> CH3 <SEP> O <SEP> CH3
<tb> <SEP> (11)
<tb> b) <SEP> RS-C <SEP> = <SEP> N-O-C- <SEP> N <SEP> + SCI, <SEP> Base <SEP> '<SEP> (I)
<tb> <SEP> I <SEP> II <SEP> I
<tb> <SEP> CH3 <SEP> 0 <SEP> CH3
<tb> <SEP> (II)
<tb>
In formula II, R has the meaning given for formula I.



   As a base z. B. in question:
Tertiary amines such as trialkylamines, pyridine and dialkylanilines; as well as inorganic bases such as hydrides, hydroxides, alkoxides and carbonates of alkali and alkaline earth metals.



   Processes a and b are carried out at a reaction temperature between −10 to 100 ° C., usually between −10 to 30 ° C., under normal pressure and in solvents or thinning agents.



   Suitable solvents or thinners are, for. B.



  Ethers and ethereal compounds such as diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran; aliphatic and aromatic hydrocarbons, especially benzene, toluene and xylenes; Ketones such as acetone and methyl ethyl ketone and cyclohexanone.



   The starting materials of the formula II themselves are already known as insecticides (cf. English and U.S. patents 1,138,347 and 3,299,137). The active compounds of the formula I according to the invention also show a very good insecticidal action, but are surprisingly more species-specific in comparison with the known compounds of the formula II. They are particularly suitable for controlling pests in cotton crops (such as, for example, Spodoptera littoralis and Heliothis virescens) and blowflies (Lucilia sericata). In addition, the compounds of formula I have in comparison with the analogs of formula II such.

  B. Lannate &commat; [CH3S-C (CH3) = N4-CO-NHCH3] surprisingly shows a significantly more favorable toxicity against warm-blooded animals.



  There is also a nematicidal effect. The insecticidal action of the compounds according to the invention can be substantially broadened by adding other insecticides and adapted to given circumstances.



   Suitable additives are, for. E.g .: organic phosphorus compounds, nitrophenols and their derivatives, formamidines, ureas, pyrethrin-like derivatives, carbamates or chlorinated hydrocarbons.



   The compounds of the formula I are used together with suitable carriers and / or additives.



  Suitable triggers and additives can be solid or liquid and correspond to the substances commonly used in formulation technology, such as B. natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or additives.



   For application, the compounds of the formula I can be processed into dusts, emulsion concentrates, granules, dispersions, sprays, into solutions or slurries in the usual formulation, which are part of general knowledge in application technology.



   The agents according to the invention are prepared in a manner known per se by intimately mixing and / or grinding compounds of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients. The connections can e.g. B. are available and used in the following processing forms:
Fixed processing forms:
Dusts, grit and granules (coating granules, impregnation granules and homogeneous granules).



     Liquid working-up forms: a) Active ingredient concentrates dispersible in water: wettable powders, pastes and emulsions; b) Solutions.



   The content of active ingredient in the compositions described above is between 0.1 and 95%.



   The following examples serve to explain the invention in more detail.



  Example 1: Preparation of means.



  I) Dusts: The following substances are used to produce a) 5% and b) 2% dust: a) 5 parts of active ingredient (compound of formula I),
95 parts of talc; b) 2 parts of active ingredient,
1 part of highly dispersed silica,
97 parts of talc.



   Like active ingredients, they are mixed and ground with the carrier substances.



  II) Granules: The following substances are used to produce 5% granules:
5 parts active ingredient,
0.25 parts epichlorohydrin,
0.25 part of Cetylpolygiykollther,
3.50 parts of polyethylene glycol, 91 parts of kaolin (grain size 0.3-0.8 mm).



   The active ingredient is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto Kaloin and the acetone is then evaporated off in vacuo.



  III) Wettable powder: To produce a) 40%, b) and c) 25% d) 10% wettable powder, the following ingredients are used: a) 40 parts of active ingredient,
5 parts of lignin sulfonic acid sodium salt,
1 part dibutylnaphthalenesulfonic acid sodium salt,
54 parts of silica; b) 25 parts of active ingredient
4.5 parts calcium lignosulfonate,
1.9 parts of champagne chalk / hydroxyethyl cellulose mixture (1:

   1),
1.5 parts of sodium dibutyl naphthalene sulfonate,
19.5 parts of champagne chalk,
28.1 parts of kaolin; c) 25 parts of active ingredient,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
1.7 parts of champagne chalk / hydroxyethyl cellulose mixture (1: 1),
16.5 parts kieselguhr,
46 parts of kaolin; d) 10 parts of active ingredient,
3 parts mixture of sodium salts of saturated fatty alcohol sulfates,
5 parts of naphthalene sulfonic acid / formaldehyde mondenate,
82 parts of kaolin.



   The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to form suspensions of the desired concentration.



  IV) Emulsifiable concentrates: The following substances are used to produce a) 10% and b) 25% emulsifiable concentrate: a) 10 parts of active ingredient,
3.4 parts epoxidized vegetable oil,
3.4 part of a combination emulsifier, consisting of fatty alcohol polyglycol ether and alkylarylsulfonate
Calcium salt,
40 parts of dimethylformamide,
43.2 parts of xylene; b) 25 parts of active ingredient,
2.5 parts epoxidized vegetable oil,
10 parts of an alkylalryl sulonate / fatty alcohol polyglycol ether mixture,
5 parts of dimethylformamide,
57.5 parts of sylol.



   Such concentrates can be diluted with water to produce emulsions of the desired concentration.



  V) Spray: To produce a) 5% and b) 95% spray, the following ingredients are used: a) 5 parts of active ingredient,
1 part epichlorohydrin,
94 parts of gasoline (boiling point 160-190 C); b) 95 parts of active ingredient,
5 parts of epichlorohydrin.



   Example 2 Preparation of bis-10- (1-methylthioithylimino) -N-methylcarbamic acid] - N, N'-sulfil:
32.4 g of 1- (methylthio) ethylideneamino-N-methylcarbamate are dissolved in 100 ml of tetrahydrofuran and 50 ml of benzene. 15.8 g of pyridine are added to this solution, 13.5 gS2Cl2 are added dropwise at 0 to 6 ° C., the reaction is stirred at this temperature for 10 hours and suction filtered. The residue is washed on the suction filter with water, dried and recrystallized from methyl ethyl ketone. Colorless crystals of the compound of the formula are obtained
EMI2.1
  (Compound (a)) with a melting point of 169-170 C.



   The following compounds are also prepared in an analogous manner: b) bis [O- (1-ethylthioethylimino) -N-methylcarbamic acid] - N, N'-sulfide: mp 136-139 C.



   312 c) bis [0 (1-n-pentylthioethylimino) -N-methylcarbamic acid] - N, N'-sulfide: m.p. 117'-119 'C.



   Example 3 A) Insecticidal feed poison action: Spodoptera Littoralis
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 covering had dried on, the plants were with
L3 instar larvae of the species Spodoptera littoralis are occupied.



   Two plants were used per test compound, and the kill achieved was evaluated after 2, 4, 24 and 48 hours. The experiment was carried out at 24 C and 60% relative humidity.

 

   Results:
Compound% destruction (according to example 2) ........ Hours



   2 4 24 48 a) 100 100 100 100 b) 90 90 90 100 B) Insecticidal food poison effect: Heliothis virescens
With the same procedure using larvae of the species Heliothis virescens, the test method described in Example 2A) was repeated.



  Results: Connection% kill after hours.



   2 4 24 48 a) 90 90 100 100 b) 60 90 100 100 C) Insecticidal effect: Chilo suppressalis
6 rice seedlings of the Caloro variety were grown in plasma pots so that their roots were matted to form a disc. The roots were in a solution containing 800, 200 or 100 ppm. immersed in the compound to be tested and allowed to drain. Then 5 test animals (larvae of the species Chilo suppressalis in the L2 stage) were each placed in a pot and the treated plants were placed on top.

 

   One plant was used per test substance and per concentration and a percentage evaluation of the destruction achieved took place after 5 days. The experiment was carried out at 24 C and 70% relative humidity.



  Results: Compound% kill at .... ppm.



   100 200 800 a) 100 100 100 b) 100 100 100

 

Claims (1)

PATENT CLAIM I. Antiseptic agents containing a compound of the formula I as the active component EMI3.1 wherein R is a C -C alkyl group. SUBCLAIMS 1. Means according to claim I containing a compound of the formula I in which R is a methyl or ethyl group. 2. Means according to dependent claim 1 containing bis- [O- (1 methylthioethylimino) -N-methyl-carbamic acid] -N, N'-sulfide. 3. Agent according to dependent claim 1 containing bis- [O- (1 äthylthioäthylimino) -N-methyl-carbamic acid] - N, N '-sulfide. PATENT CLAIM II. Use of an agent according to claim I for combating insects. SUBClaim 4. Use remiss claim II for combating plant-shedding insects.