Insectoacaricidic agent

专利摘要:
Compounds of the formula (I) wherein R1, R2 and R3 independenely of one another are hydrogen, halogen, methyl or ethyl, R4 is C1-C8-alkyl, C3-C5-cycloalkyl or (C3-C6- cycloalkyl)-methyl, and eitheri) R5 is hydrogen, C1-C8-alkyl, C1-C4-alkoxy, C3-C6- cycloalkyl or (C3-C6-cycloalkyl)-methyl, whilst R6 is C1-C8-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl or (C3-C6-cycloalkyl)-methyl, or ii) R5 and R6 together with the nitrogen atom to which they are attached represent a 5- or 6-mem-bered heterocyclic ring optionally substituted by one or more C1-C4-alkyl groups and optionally including an oxygen or sulphur atom within the ring system, posess valuable insecticidal and in particular acaricidal properties.
公开号:SU791197A3
申请号:SU762378585
申请日:1976-07-08
公开日:1980-12-23
发明作者:Бегер Манфред；Драбек Иозеф
申请人:Циба-Гейги Аг (Фирма)；
IPC主号:

专利说明:

The invention relates to agricultural pest control chemicals, specifically to the use of an insecticidal and acaricidal agent based on amidine derivatives. Insecticide II is known, the active ingredient of which is p- (N-methylthiomethylaminomethylidene) -amino-phenyl ester of N-methylcarbamic acid. The closest in chemical structure to the proposed invention is an insecticide and an acaricide based on N- (4-chloro-2-methylphenyl) -y, N-dimethyl formamidine 2. However, these pesticides have insufficient activity at low concentrations. The purpose of the invention is to expand the arsenal of plant protection products having a high insecticoacaricidal activity at low concentrations of the active substance. This goal is achieved using 1-phenyl-1, 3,5,7-tetraz-4-sulf-hept-1-one derivatives of the general formula I -methyl, chlorine or bromine; -methyl, n-butyl, n-hexyl, n-octyl, cyclopropylmethyl, cyclohexyl and cyclopropyl; hydrogen, methyl, n-propyl, n-butyl, n-octyl, cyclohexyl, cyclopropylmethyl, and methoxy; hydrogen, methyl, n-propyl and n-octyl; . together with the azokotor atom, they are bound to form a lidinyl, morphonyl, or methylmorphonyl ring, 0.5 to 95.5 wt.%. of the general formula I by the semi-interaction of formamidines with evinasulfenyl halides. The action is carried out at a temperature ranging from -20 ° C to + 30 ° C, in an inertMoV solvent in the presence of a base.
In this way, 1- (2-methyl-4-chlorophenyl) -3,5,7-trimethyl-1, 3,5,7-tetraz-4-sulfa-oct-1-ene-6-one is obtained (soy ).
To a solution of 18.3 g of methyl N- (4-chloro-2-methyl-phenyl) -formamidine in 200 ml of tetrahydrofuran was added 10.5 g of triethylamine. Then, with stirring and cooling with ice
16.9 g of trimethylurea sulphenyl chloride are added dropwise.
The reaction mixture is stirred for another half hour at room temperature, the triethylamine hydrochloride is filtered off, evaporated and dried in the form of a yellow oil with a refractive index of 1.5820 at -20 ° C.
The following compounds of general formula I are prepared in a similar manner, as shown in Table 1.
T a
faces
23 CHj CH. -CHj-CH-O-CH-CH, -CH, 24 CH, 78-79 71-73 Compounds of general use I are common: powdered preparations, emulsion concentrates, granules, dispersions. The content of the active substance in these preparations is 0.595, 5 wt.%. The biological activity of the proposed compounds is illustrated by the following examples. Example 1. Acaricidal action. Primary leaflets of plants of the common bean 16 hours before the experiment for the acaricidal effect are infected with an infested piece of a leaf from the mass growth of Tetranychus urtical (RR-sensitive) or Tetranychus cinnabarius (OP-tolerant). Tolerance (endurance) refers to compatibility with diazinon. The transitioned mobile stages are polluted from the chromatographic
Continued table. 1 itel emulsified with a preparation containing 800 MD; 400 ppm, 00 ppm, or 100 ppm test compound. After 24 hours and again after 7 days, adults and larvae (all moving stages) are visually assessed on living and dead individuals. There is one concentration and one test plant species per substance to be tested. In the process of leakage,: no experience of the plant is kept in the offices of the greenhouse at. Compound A was used as the comparative substance: Cg- / -M CE-fi. The test results are shown in Table 2. table 2
Example 2. Insecticidal action.
6 sprouts of Caloro rice variety are pulled out of plastic pots so that their root system is entangled in a circle. The roots are immersed in 0.08, 0.04, 0.02, or 0.01% solution of the biologically active substance and left to drip. Then, 5 test subjects are placed in each pot.
Continued tabl, g i
animals (Chilo Suppressalis larvae in the L2-stage) and treated plants are also placed there.
The assessment in lrocents of the achieved mortality is carried out after 5 days and the experiment is carried out at 24 ° C and 70% relative air humidity.
The results of the experiments are given in table.3.
100% killing at ppm 0.04 0.02 0.08 0.02
Connection No.
100% killing at ppm 0.08. 0.08 0.04 0.08
Connection No.
100% killing at ppm iD, 02. 0.08 0.02 0.08
Compound,

权利要求:
Claims (1)
[1]
100% killing at a ppm of 0.01 0.08 0.08 0.08 Thus, the proposed compounds have a high insecticidal and acaricidal activity at low concentrations. Invention The insecticide acaricidal agent containing the active principle on the basis of the derivatives of formamidine and additives selected from the group of: carrier, diluent, filler, which has been found in order to strengthen the insecticoacaricidal effect. as pho amidine derivatives of the compound of the general formula I S, - // h Rt is methyl, chloro or br; R is methyl, n-butyl, n-hexyl, n-octyl, cyclopropylmethyl, cyclohexyl and cyclopropyl; Rn is hydrogen, methyl, n-propyl, n-butyl, methyl, cyclohexyl, cyclopropylmethyl, and methoxy; R is hydrogen, methyl, npropyl and n-octyl;
Table 3
10 12
13 14 15 16
17 21 22 29 and R, together with the nitrogen atom, orym, they are bound to form lidinyl, morphonyl or immethyl morphonyl rings of 0.5-95.5 wt.%. Priority signs: 4.07.75 when R is methyl, chlorine; when Rg is methyl, n-octyl, n-butyl ;. when R is hydrogen, methyl, n-propyl, n-octyl, methoxy group; when R is methyl, n-propyl, n-octyl; together with the nitrogen atom form a pyrrolidinyl, morphonyl or 3,5-dimethylmorphonyl ring. 02.02.76 when RJ is n-butyl; -hydrogen. at 3.06.76 when bromine; at R2, cyclopropylmethyl, cyclohexyl, n-hexyl, cyclopropyl; with poison - cyclohexyl, cyclopropylmethyl. Sources of information that are taken into account in the examination. Patent of the USSR No. 292258, A 01 N 9/20, published. 1971. N.N. Melnikov Chemistry and techno pesticides. M., 1974, p. 203 totip).

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引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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US3853966A|1970-11-09|1974-12-10|G Kohn|N-chlorothio ureas|

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US3857883A|1972-05-08|1974-12-31|Chevron Res|N-chlorothio urea production|

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US3947591A|1975-05-07|1976-03-30|The Upjohn Company|Pesticidal N,N"-thio and dithio bis|DE2737606A1|1977-08-20|1979-03-01|Bayer Ag|ARYL-N-ALKYL-CARBAMATE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES|

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US4369189A|1980-12-10|1983-01-18|Union Carbide Corporation|Novel unsymmetrical formamidine-sulfenylated carbamate compounds|

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AU572825B2|1983-03-03|1988-05-19|Fmc CorporationLimited|Inhibition of corrosion and scale formation of metal surfaces|

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CA1339745C|1984-04-10|1998-03-17|Martin Anderson|Pesticidal benzoylurea compounds|

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JPS62290780A|1986-06-09|1987-12-17|Sunstar Giken Kk|One-pack chloroprene adhesive|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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CH967475A|CH612421A5|1975-07-24|1975-07-24|Pesticide comprising a urea as active ingredient|

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CH190976|1976-02-17|

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CH702076|1976-06-03|

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