CH623992A5 - A pesticide - Google Patents

Abstract

A pesticide which contains, as active ingredient, a compound of the formula I <IMAGE> in which R1, R2 and R3 in each case denote hydrogen, C1-C4-alkyl or halogen, and R4 denotes methyl or ethyl. The use of these compositions for controlling insects, representatives of the order Acarina, phytopathogenic nematodes and fungi is described.

Description

       

  
 

** WARNING ** beginning of DESC field could overlap end of CLMS **.

 



   PATENT CLAIMS
1. A pesticide, which as an active component is a compound of the formula
EMI1.1
 contains, wherein R1, R2 and R3 each represent hydrogen, C14-alkyl or halogen and R4 is methyl or ethyl.



   2. A composition according to claim 1, wherein in the active component R1, R2 and R3 each represent hydrogen, methyl, chlorine or bromine and R4 is methyl or ethyl.



   3. A composition according to claim 2, which as the active component is the compound of the formula
EMI1.2
 contains.



   4. An agent according to claim 2, which as the active component is the compound of the formula
EMI1.3
 contains.



   5. Use of an agent according to claim 1 for controlling various types of animal and vegetable pests.



   6. Use according to claim 5 for controlling insects and representatives of the order Akarina.



   7. Use according to claim 5 for combating phytopathogenic nematodes.



   8. Use according to claim 5 for combating phytopathogenic fungi.



   The present invention relates to a pesticide which, as the active component, is a phenylformamide of the formula
EMI1.4
 contains, wherein R1, R2 and R3 each represent hydrogen, C1-C4-alkyl or halogen and R4 is methyl or ethyl.



   Halogen here means fluorine, chlorine, bromine and / or iodine, in particular chlorine and / or bromine. The alkyl groups suitable for R1, R2 and R3 can be straight-chain or branched. Examples of such groups are: methyl, ethyl, propyl, isopropyl, n-, i-, sec-, tert-butyl.



   Because of their action, preference is given to phenylformamidines of the formula I in which R1, R2 and R3 are each hydrogen, methyl, chlorine or bromine and R4 is methyl or ethyl.



   The phenylformamidines of the formula I can be prepared by processes known per se, for example by using a compound of the formula
EMI1.5
 in the presence of an acid-binding agent with a compound of the formula
EMI1.6
 implements.



   In the formulas II and III, R1 to R4 have the meaning given for the formula I and Hal represents a halogen atom, in particular chlorine or bromine. Acid-binding agents are, in particular, tertiary amines, such as trialkylamines and pyridine, furthermore hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals and alkali metal alcoholates such as, for. B. Potassium t.butylate and sodium methylate into consideration. The process is carried out at a reaction temperature between -20 and 30 C, at normal or elevated pressure and, if appropriate, in an inert solvent or diluent or in an excess of the acid-binding agent used.



   Suitable solvents or diluents are e.g. B. ether and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuran; Amides such as N, N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform and chlorobenzene; Nitriles such as acetonitrile; Dimethyl sulfoxide and ketones such as acetone and methyl ethyl ketone.



   The starting materials of the formulas II and III are known or can be prepared analogously to known methods.



   The phenylformamidines of the formula I are suitable for controlling various types of animal and vegetable pests. They have nematicidal properties and can be used, for example, to control plant pathogenic nematodes. They are also suitable for combating viruses, bacteria and phytopathogenic fungi. In particular, the phenylformamidines of the formula I, however, have an outstanding action against insects and representatives of the order Akarina. The phenylformamidines of the formula I are therefore outstandingly suitable for combating



  phytopathogenic mites and ticks, for example from the genera Tetranychus and Panonychus and the families Dermanyssidae and Ixodidae, and for controlling insects, for. B. the families Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduvidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysom Stomoxydae, Trypedidae, Muscidae, Calliphoridae and Pulicidae.



   The phenylformamidines of the formula I are particularly suitable for combating plant-damaging insects, in particular plant-damaging insects in ornamental and useful plants, in particular in cotton crops (e.g. against Spodoptera littoralis and Heliothis virescens) and vegetable crops (e.g. against Leptinotarsa decemlineata and Myzus persicae).



   The phenylformamidines of the formula I also have a very favorable action against flies such as. B. Musca domestica and mosquito larvae. The acaricidal or insecticidal effect can be significantly broadened by adding other insecticides and / or acaricides and adapted to the given circumstances. As additives are such. B. org. Phosphorus compounds; Nitrophenols and their derivatives; other formamidines; Ureas; pyrethrin-like compounds as well as carbamates and chlorinated hydrocarbons. The compounds of the formula I are particularly advantageously combined with substances which have a reinforcing effect. Examples of such connections include. a .: piperonyl butoxide, propynyl ether, propynyl oximes, propynyl carbamates and propynyl phosphonates.



   The compounds of formula I can be used alone or together with suitable carriers and / or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. B. natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers. For application, the compounds of the formula I can be processed into dusts, emulsion concentrates, granules, dispersions, sprays, into solutions or slurries in customary formulations which are common knowledge in application technology. Furthermore, cattle dips, i.e. Cattle baths, and spray races, d. H. To mention spray courses in which aqueous preparations are used.



   Agents according to the invention are prepared in a manner known per se by intimately mixing and / or grinding active ingredients of the formula I with the suitable carriers, optionally with the addition of dispersing agents or solvents which are inert to the active ingredients. The active ingredients can be present and used in the following processing forms: Solid processing forms: dusts, scattering agents, granules (coating granules, impregnation granules and homogeneous granules); Liquid processing forms a) active ingredient concentrates dispersible in water:
Wettable powders, pastes, emulsions; b) solutions.



   The content of active ingredient in the agents described above is between 0.1 to 5) 95%.



   The active ingredients of the formula I can be formulated, for example, as follows: dusts:
The following substances are used to produce a) 5 (4-part and b) 2 '-winning dusts: a) 5 parts of active ingredient,
95 parts talc; b) 2 parts of active ingredient,
1 part of highly disperse silica, 97 parts of talc.



   The active ingredients are mixed and ground with the carriers.



  Granules:
The following substances are used to produce 5% granules:
5 parts of active ingredient,
0.25 parts of epoxidized vegetable oil,
0.25 parts of cetyl polyglycol ether,
3.50 parts of polyethylene glycol,
91 parts of kaolin (grain size 0.3-0.8 mm).



   The active substance is mixed with epoxidized vegetable oil and dissolved with 6 parts of acetone, whereupon polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and the acetone is then evaporated in vacuo.



  Spray powder:
The following constituents are used to produce a) 40%, b) and c) 25%, d) 10% wettable powder: a) 40 parts of active ingredient,
5 parts of sodium lignosulfonic acid,
1 part of dibutylnaphthalenesulfonic acid sodium salt,
54 parts of silica; b) 25 parts of active ingredient,
4.5 parts of calcium lignin sulfonate,
1.9 parts champagne chalk / hydroxyethyl cellulose mixture (1: 1),
1.5 parts of sodium dibutyl naphthalenesulfonate,
19.5 parts of silica,
19.5 parts of champagne chalk,
28.1 parts kaolin; c) 25 parts of active ingredient,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
1.7 parts of champagne chalk / hydroxyethyl cellulose mixture 1),
8.3 parts of sodium aluminum silicate,
16.5 parts of diatomaceous earth,
46 parts of kaolin;

   d) 10 parts of active ingredient,
3 parts mixture of the sodium salt of saturated fat alcohol sulfates,
5 parts of naphthalenesulfonic acid / formaldehyde condensate sat,
82 parts of kaolin.



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



  Emulsifiable concentrates:
The following substances are used to prepare a) 10%, b) 25% and c) 50% emulsifiable concentrate: a) 10 parts of active ingredient,
3.4 parts of epoxidized vegetable oil,
3.4 parts of a combination emulsifier consisting of
Fatty alcohol polyglycol ether and alkylarylsulfonate
Calcium salt,
40 parts of dimethylformamide,
43.2 parts xylene; b) 25 parts of active ingredient,
2.5 parts of epoxidized vegetable oil,
10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture,
5 parts of dimethylformamide,
57.5 parts of xylene, c) 50 parts of active ingredient,
4.2 parts of tributylphenol polyglycol ether,
5.8 parts of calcium dodecylbenzenesulfonate,
20 parts of cyclohexanone,
20 parts of xylene.



   Such concentrates can be diluted with
Water emulsions of any desired concentration can be prepared.



  Spray agent:
The following constituents are used to produce a) 5% and b) 95% spray: a) 5 parts of active ingredient,
1 part epoxidized vegetable oil,
94 parts of gasoline (boiling limits 16> 190 C); b) 95 parts of active ingredient,
5 parts of epoxidized vegetable oil.



   example 1
Preparation of 1 - (2-methyl-4-chlorophenyl) -
3,5-dimethyl-1,3,5-triaza-4-sulfa
5-O, O-dimethyl-phosphonyl-hex-1-ene
9.5 g of triethylamine are added to a solution of 16.6 g of N-methyl-N '- (4-chloro-2-methylphenyl) formamidine in 100 ml of methylene chloride. With constant stirring, 18.5 g of the compound of the formula slowly become at about 0 ° C
EMI3.1
 added dropwise, then stirred for another half an hour without cooling and then added 100 ml of water. After evaporation of the previously dried methylene chloride solution in a high vacuum, the compound of the formula is obtained
EMI3.2
 as a yellow oil with a refractive index of n20 = 1.5624.



   The following connections are also made in an analogous manner:
EMI3.3

Example 2
A. Insecticidal food poison effect
Cotton plants were sprayed with a 0.05% aqueous active ingredient emulsion (obtained from a 10% emulsifiable concentrate).



   After the covering had dried on, the cotton plants were each populated with Spodoptera littoralis and Heliothis virescens larvae Ls. The trial was at 24 C and 60%. relative humidity.



   In the above test, the compounds according to Example 1 showed a good insecticidal feeding poison effect against Spodoptera and Heliothis larvae.



   B. Systemic insecticidal activity
To determine the systemic effect, rooted bean plants (Vicia faba) were placed in a 0.01% strength aqueous active ingredient solution (obtained from a 10% strength emulsifiable concentrate). After 24 hours, aphids (Aphis fabae) were placed on the aerial plant parts. The animals were protected from contact and gas effects by a special device. The test was carried out at 24 C and 70 echo relative humidity. The compounds according to Example 1 showed systemic insecticidal activity against Aphis fabae in the above test.



   Example 3
Effect against Chilo suppressalis
6 rice plants of the Caloro variety were transplanted into plastic pots with an upper diameter of 17 cm and grown to a height of about 60 cm. The infestation with Chilo suppressalis larvae (L1; 3-4 mm long) took place in the paddy water 2 days after the addition of the active substance in granular form (application rate 8 kg of active substance per hectare). The insecticidal activity was evaluated 10 days after the addition of the granules.



   The compounds according to Example 1 showed good activity in the above test against Chilo suppressalis.



   Example 4
Acaricidal effects
Phaseolus vulgaris (plants) was covered with an infested leaf piece from a mass cultivation of Tetranychus urticae 12 hours before the test for acaricidal activity. The overflowed moving stages were sprayed with the emulsified test preparations from a chromatography atomizer in such a way that the spray liquor did not run off.



  After 2 to 7 days, larvae, adults and eggs were evaluated under the binocular for living and dead individuals and the result was expressed in percent. During the holding period, the treated plants stood in greenhouse cabins at 25 C.



   The compounds according to Example 1 worked very well in the above test against adults, larvae and eggs of Tetranychus urticae.



   Example 5
Effect against soil nematodes
To test the action against soil nematodes, the active ingredients were given to the soil infected by root cell nematodes (Meloidogyne arenaria) and mixed intimately. In one test series, tomato seedlings were planted immediately afterwards in the prepared soil and in another test series, tomatoes were sown after a waiting period of 8 days.



   To assess the nematicidal activity, the galls present at the roots were counted 28 days after planting or after sowing. In this test, the active ingredients according to Example 1 showed a good action against Meloidogyne arenaria.



   Example 6
Effect against ticks
A. Rhipicephalus bursa
5 adult ticks and 50 tick larvae were counted in a glass tube and immersed for 1 to 2 minutes in 2 ml of an aqueous emulsion from a dilution series with 100, 10, 1 or 0.1 ppm test substance. The tube was then closed with a standardized cotton ball and turned upside down so that the active ingredient emulsion could be absorbed by the cotton wool.



   The evaluation was carried out after 2 weeks for the adults and after 2 days for the larvae. There were 2 repetitions for each attempt.



   B. Boophilus microplus (larvae)
With an analog dilution series as in test A) with 20 sensitive resp. OP-resistant larval experiments were carried out. (The resistance relates to the tolerance of diazinon). The compounds according to Example 1 were active in these tests against adults and larvae of Rhipicephalus bursa and sensitive resp. OP-resistant larvae from Boophilus microplus.

 

   Example 7
Effect against Erysiphe graminis on Hordeum vulgare
Barley plants of about 8 cm in height were sprayed with a spray mixture (0.05% active substance) prepared from wettable powder of the active ingredient. After 48 hours, the treated plants were dusted with conidia of the fungus. The infected barley plants were placed in a greenhouse at about 22 ° C. and the fungal attack was assessed after 10 days.



  The compounds according to Example 1 acted against Erysiphe graminis in this test.


    

Claims (8)

 PATENT CLAIMS 1. A pesticide, which as an active component is a compound of the formula EMI1.1  contains, wherein R1, R2 and R3 each represent hydrogen, C14-alkyl or halogen and R4 is methyl or ethyl.  2. A composition according to claim 1, wherein in the active component R1, R2 and R3 each represent hydrogen, methyl, chlorine or bromine and R4 is methyl or ethyl.  3. A composition according to claim 2, which as the active component is the compound of the formula EMI1.2  contains.  4. An agent according to claim 2, which as the active component is the compound of the formula EMI1.3  contains.  5. Use of an agent according to claim 1 for controlling various types of animal and vegetable pests.  6. Use according to claim 5 for controlling insects and representatives of the order Akarina.  7. Use according to claim 5 for combating phytopathogenic nematodes.  8. Use according to claim 5 for combating phytopathogenic fungi.  The present invention relates to a pesticide which, as the active component, is a phenylformamide of the formula EMI1.4  contains, wherein R1, R2 and R3 each represent hydrogen, C1-C4-alkyl or halogen and R4 is methyl or ethyl.  Halogen here means fluorine, chlorine, bromine and / or iodine, in particular chlorine and / or bromine. The alkyl groups suitable for R1, R2 and R3 can be straight-chain or branched. Examples of such groups are: methyl, ethyl, propyl, isopropyl, n-, i-, sec-, tert-butyl.  Because of their action, preference is given to phenylformamidines of the formula I in which R1, R2 and R3 are each hydrogen, methyl, chlorine or bromine and R4 is methyl or ethyl.  The phenylformamidines of the formula I can be prepared by processes known per se, for example by using a compound of the formula EMI1.5  in the presence of an acid-binding agent with a compound of the formula EMI1.6  implements.  In the formulas II and III, R1 to R4 have the meaning given for the formula I and Hal represents a halogen atom, in particular chlorine or bromine. Acid-binding agents are, in particular, tertiary amines, such as trialkylamines and pyridine, furthermore hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals and alkali metal alcoholates such as, for. B. Potassium t.butylate and sodium methylate into consideration. The process is carried out at a reaction temperature between -20 and 30 C, at normal or elevated pressure and, if appropriate, in an inert solvent or diluent or in an excess of the acid-binding agent used.  Suitable solvents or diluents are e.g. B. ether and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuran; Amides such as N, N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform and chlorobenzene; Nitriles such as acetonitrile; Dimethyl sulfoxide and ketones such as acetone and methyl ethyl ketone.    The starting materials of the formulas II and III are known or can be prepared analogously to known methods.  The phenylformamidines of the formula I are suitable for controlling various types of animal and vegetable pests. They have nematicidal properties and can be used, for example, to control plant pathogenic nematodes. They are also suitable for combating viruses, bacteria and phytopathogenic fungi. In particular, the phenylformamidines of the formula I, however, have an outstanding action against insects and representatives of the order Akarina. The phenylformamidines of the formula I are therefore outstandingly suitable for combating ** WARNING ** End of CLMS field could overlap beginning of DESC **.