DE2600987A1 - SCHAEDLING INHIBITOR - Google Patents

Description

■ CiBA-GEIGY

CLBA-GE [GY AG, Basel, Switzerland

Case 5-9748 / 9963/1 + 2 / =

GERMANY

Dr. F. Zumstein son. - Dr. Ξ. Ass -i-snn

Dr. R. Kcerfg .. 'org-r - Dipl.- Phys. ; t. Kolsbauer

Dipl . -Ing, tr. Klfcigssisen - Dr. F. Zurnstein jun.

Patent Attorneys β Munich 2, Bräuhausstraß © 4

Pesticides

The present invention relates to new sulfenylated ones Phenylformamidine, which have an effect against pests own processes for their production, as well as pesticides, which contain these formamidines as active ingredients and methods of combating pests using the new formamidines.

The novel phenylformamidines according to the invention have the Formula I.

R-, R2 and Rn independently of one another a hydrogen or halogen atom or a C ₁ -C ₇ -AlCyI-, C ₁ -C ₇ -AIkOXy, C ₁ -C, -alkylthio, trifluromethyl, cyano or nitro group,

609830/0928

R, a C -C, alkyl group,

Rc is an optionally halogen-substituted C, -C ^^ - alkyl group or a Co-C ₁ Q-Cycloalkyl, C, -C ₁ Q (cycloalkylalkyl) or C ₂ -C ₁₀ - (alkoxyalkyl) group, and

R, a hydrogen atom: an optionally halogen substitute

tuated C-, -C 1-4 -alkyl or C-, -C-1Q-alkoxy group; or a C ₃ -C ^ Q-cycloalkyl, Co-C ^ cycloalkyloxy, C, -C _Q - (cycloalkylalkyl) -, C ₄ -C ₁₀ - (CycloaIkylalkoxy) -, C ₂ -C ₁ Q- (AIkoxyaIky1) - or Cp -C-, "- (AIkoxyaIkoxy) group.

Of particular importance because of their action against pests,

in particular against insects and especially against representatives of the order Akarina , are compounds of the above-mentioned formula I, in which

R _{1 is} a C ₁ -C, alkyl group (in particular a methyl group) in the ortho position,

Rg is a C ₁ -C, alkyl group (especially a methyl group) or a halogen atom (especially a chlorine or bromine atom) in the para position,

R ~ denotes a hydrogen atom and R, denotes a methyl group while

R ₁ - and R- have the meanings already given under formula I.

and above all the compounds of the formula I are preferred,

R _{1 is} a C -C alkyl group (especially a methyl group) in the ortho position, 609830/0928

R_ is a C ₁ -C, alkyl group (especially a methyl group) or a halogen atom (especially a chlorine or
Bromine atom) in the para position,
Ro is a hydrogen atom and
R, represent a methyl group and either

i) R is an optionally halogen-substituted C ₁ -C, _Q -alky! group or a C ₃ -C ₁₀ cycloalkyl, C 1 -C 4 (cycloalkylalkyl) or C ₂ -C ₁₀ (alkoxyalkyl) group, in particular a C, -C-iQ-alkyl-, Co-C ^ -Cycloalkyl-,
C -C ₆ -CyClOaIlCyI-C ₁ -C ₉ -alkyl- or C ₁ -C ^
C ₁ -C, -alkyl group, while,
R _{7 represents} a hydrogen atom, or
ii) R ₁ . an optionally halogen-substituted one

yyyy in particular one if applicable

is halogen-substituted C ₁ -C, -alkyl group, while,
R _fi for an optionally halogen-substituted C.-C ₁₀ -alkyl or C-. -C _1rv -alkoxy group or a C ₀ -C _1n -cycloalkyl-, Co-C ^ -Cycloalkoxy-, C, -C _1Q - (cycloalkylalkyl) -, C ^ -C - (cycloalkylalkoxy), C ₃ -C ₁₀ - (alkoxyalkyl) - or C ₂ ^- C ₁ - (AIkoxyalkoxy) group in particular a C ₁ -CJ ^ alkyl, C ₁ -C alkoxy, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₂ alkyl -, C ₃ -Cg cycloalkyl

C ₁ -C alkyl or

609830/0928

C -C -alkoxy-C -C, -C -alkoxy group.

Alkyl groups in formula I can be branched or straight-chain and examples of such groups include the methyl, ethyl, n-propyl, isopropyl, η-butyl, isobutyl, sec-butyl and tert-butyl groups and for R. , - and Rg of the n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl group and their isomers into consideration. Such alkyl groups also form the alkyl portions of alkoxy, alkylthio, alkoxyalkyl and alkoxyalkoxy substituents. Furthermore, alkyl groups and alkoxy groups as R ₁ - and R 1 - can be substituted by 1 or more halogen atoms, in particular by 1 to 4 chlorine and / or bromine atoms.

"Cycloalkyl groups" are the cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl group, especially the cyclopropyl, cyclohexyl and cyclooctyl group. These groups also form the cycloalkyl portion of cycloalkylalkyl and cycloalkylalkoxy groups such as the cyclopropylmethyl, 2-cyclopropylethyl, Cyclohexylmethyl-, Cyclooctylmethyl-, 4-Cyclopropyl-n-butyl-, 4-cyclopropyl-3-methyl-n-butyl, cyclopropylmethoxy, cyclohexylmethoxy and cyclooctylmethoxy groups.

Halogen atoms are to be understood as meaning the fluorine, chlorine, bromine and iodine atom, in particular the chlorine or bromine atom.

The new sulfenylated phenylformamidines of the formula I are

609830/0928

obtained by methods known per se in that, for example, a compound of the formula II

N = CH - N ^

L. ^H

in the presence of a bath containing a compound of formula IJI

HaI-S-N

\ (III)

^CR fi

reacted, where in the formulas II and III R ₁ to R ^ have the meanings already given under formula I and "!! al" stands for an Ilalogenatom, in particular a chlorine or bromine atom.

The process is carried out at a reaction temperature between -20 and 30 C, at normal or elevated pressure and preferably carried out in a solvent or diluent which is inert towards the reactants. Suitable solvents or diluents for this reaction are e.g. Ether and ethereal compounds, such as diethyl ether, di-iso ~ propyl ether, dioxane, dimethoxyethane and tetrahydrofuran: Amides such as N, N-di-alkylated carboxamides; aliphatic and 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.

In particular, tertiary amines, such as triethyl-

609830/0928

amine, dimethylaniline, pyridine, picolines and lutidines, furthermore Hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals as well as alkali metal alcoholates such as e.g.

Potassium t-butylate and sodium methylate are considered.

The derivatives of the formulas used as starting materials

II and III are known or can be known per se

Methods are made.

The compounds of formula I have a broad biocidal range Effect on and can be used to combat various plant and animal pests,

e.g. as acaricides, insecticides, ectoparasiicides,

as well as plant regulators or herbicides. They are particularly suitable for combating acarids, for example of the Fcimilieii: Ixodidae, Argasidae, Tetranychidae and Dermanysidae, it being worth mentioning that compounds of the formula I in which R _{1 is} o-methyl, R ^ p-chlorine and R ~ are hydrogen Excellent long-term action against larvae and adults, while those in which R, ο-methyl, R «ρ-methyl and R» represent hydrogen achieve a remarkable effect primarily as ovicides.

Furthermore, the compounds of the formula I have a beneficial action against insects which are harmful to plants and animals and can, for example, according to the invention for combating

of insects of the families: Acrididao, Blattidae, Gryllidae, GryllotalpidacTettigoniidae, - Cimicidae, Pyrrhocoridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseudococcidae, Chrysomelidae, Coccinellidae, Bruchidae, Scarabaeidae,

609830/0928

Dermestidae, Tenebrionidae, Curculionidae, Tineidue, Noctuidae, Lymantriidae, Pyralidae, Galleridae, Culicidae, Tipulidae, Stomoxydae, Muscidae, Calliphoridae, Trypetidae and Pulicidae and above all to control aphids (e.g. Hyzus per-sicae). So are the Compounds of the formula I, in particular for combating insects which are harmful to plants in crops of fruit, vegetables and ornamental plants.

The acaricidal or insecticidal effect can be achieved by adding other insecticides and / or acaricides widen it considerably and adapt it to the given circumstances.

Examples of suitable additives are: organic phosphorus compounds; Nitrophenols and their derivatives; Formamidine; Ureas; pyrethrin-like compounds; Carbamates and chlorinated Hydrocarbons.

The compounds of the formula I can be used alone or together with suitable carriers and / or additives can be used. Suitable carriers and aggregates can be solid or liquid and correspond to the substances commonly used in formulation technology, such as natural or regenerated

Substances, solvents, dispersants, wetting, adhesive, thickening, Binders and / or fertilizers.

For application, the compounds of the formula I can be used Dusts, emulsion concentrates, granules, dispersions, sprays, to solutions or slurries in the usual way Formulation that is used in application technology for general

609830/0928

know belong, be processed.

The 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 dispersants or solvents which are inert towards the active ingredients. The active ingredients can be present and used in the following working-up forms: Solid
Forms of processing: dust, grit,

Granulates, coated granulates, impregnation granulates and homogeneous egg granulates ; Liquid
Forms of processing:

a) dispersible in water

Active ingredient concentrates: wettable powder,

Pastes, emulsions;

b) Solutions

The content of active ingredient in the agents described above is between 0.1 and 95%, it should be mentioned that with the application from the aircraft or by means of other suitable application devices also higher concentrations

can be used.

The active ingredients of the formula I can, for example, as follows

be formulated:

609830/0928

Dusts The following substances are used to produce a) 5% and b) 2% dust:

a) 5 parts of active ingredient, 95 parts of talc;

b) 2 parts of active ingredient,

1 part of highly disperse silica, 97 parts of talc.

The active ingredients are mixed with the carriers and marry.

Granules: The following substances are used to produce 5% granules:

5 parts of active ingredient, 0.25 parts of epichlorohydrin, 0.25 part of cetyl polyglycol ether,

3.50 parts of polyethylene glycol, 91 parts of kaolin (grain size 0.3-0.8 mm).

The Aktivoubstanz is mixed with epichlorohydrin and with 6 parts of acetone dissolved, then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and then the acetone is evaporated in the vacuum.

Spray powder : To produce a) 40% / b) and c) 257oigert and d) 10% spray powder, the following ingredients are used:

609830/0928

a) 40 parts active ingredient /

5 parts of lignin sulfonic acid, sodium salt, 1 part of 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 silica, 19.5 parts champagne chalk, 28.1 parts kaolin?

c) 25 parts of active ingredient

2.5 parts isooctylphenoxy-polyethylene-ethanol, 1.7 parts Chairtpag-ne chalk / hydroxyethyl cellulose

Mixture (1: 1), 8.3 parts sodium aluminosilicate,

16.5 parts of kieselguhr, 46 parts of kaolin;

d) 10 parts of active ingredient,

3 parts mixture of the sodium salts of saturated

Fatty alcohol sulfates _f
5 parts naphthalenesulfonic acid / formaldehyde condensate

sat,

82 parts of kaolin.

The active ingredients are mixed with the additives in suitable mixers intimately mixed and ground on appropriate mills and rollers. You get wettable powder, which with water to make suspensions of any desired concentration

609830/0928

-Λ λ *

let it dilute.

Emulsifiable concentrates: The following substances are used to produce a) 10% b) 25% and c) 50% emulsifiable concentrate:

a) IO parts active ingredient,

3.4 parts epoxidized vegetable oil,

3.4 parts of a combination emulsifier, consisting of from fatty alcohol polyglycol ether and alkylarylsulfonate calcium salt, Parts of dimethylformamide and 43.2 parts of xylene;

b) 25 parts of active ingredient,

2.5 parts epoxidized vegetable oil,

10 parts of an alkyl aryl sulfonate / fatty alcohol poly

glycol ether mixture, 5 parts of dimethylformamide and 57.5 parts of xylene;

c) 50 parts of active ingredient,

4.2 parts of tributylphenol polyglycol ether, 5.8 parts of calcium dodecylbenzenesulfonate, Parts cyclohexanone, parts xylene.

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water. 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 gasoline (boiling point 16O-19O ° C)

609830/0928

b) 95 parts of active ingredient,

5 parts of epichlorohydrin.

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

609830/0928

example 1

A) Production of 1,3, S- phenyl) -B-

To a solution of 18.2 g of N-methyl-N'- (4-chloro-2-methylphenyl) formamidine in 60 ml of pyridine, slowly ground 14.0 g of N- with constant stirring at 0 ° to 10 ° C. Methyl acetamidosulfenyl chloride was added dropwise. The mixture is stirred for a further 20 minutes at this temperature, then the excess pyridine is removed ^{at 1 mm Hg pressure and 50 ° C.} The semicrystalline residue is mixed with 150 ml of toluene and 100 ml of ice water, the toluene phase is washed with a further 3 times 80 ml of ice water, dried over sodium sulfate, evaporated and finally dried in a high vacuum at 40 °.

The compound of the formula is obtained

(Compound No. 1) COCH ₃

20th

as a yellow oil with a refractive index of n _Q : 1.5933.

609830/0928

B) production of 1,3,5-

10.2 g of triethylamine are added to a solution of 18.2 g of N-methyl-N ¹ - (4-chloro-2-methylphenyl) formamidine in 200 ml of tetrahydrofuran. With constant stirring, 17.0 g of N-formyl-methoxyethylamine-sulfenyl chloride are slowly added dropwise at 5 ° to 15 ° C., then the mixture is stirred for 30 minutes at room temperature, the triethylamine hydrochloride is filtered off and the filtrate is evaporated and finally dried in a high vacuum.

The compound of the formula is obtained

^CH 3
-S ^ CH.

Cl- / // "N = ^CH - \ ^ CH ₂ CH ₂ -OCH ₃ (Compound No. 2)

'CHO

as a yellow oil with a refractive index of η 1.5781.

C) The following compounds of the formula Ia ₅ Ib and Ic were also prepared in an analogous manner:

6 0 9830/0928

CH

Cl

- E = CH-

CH ₃ S - N

^R 5

COR,

(la)

link
No. ^R 5 ^R 6 Physical data 3 CH ₃ - H n ^ ⁰ : 1.6008 4th C ₂ H ₅ - H n £ °: 1.5880 5 Cn) C ₃ H ₇ - H 6th Ci) C ₃ H ₇ - H n ^ °: 1.5815 7th Ci) C ₄ H ₉ - H 8th CH ₃ - CH ₃ O- n ^ ⁰ : 1.5780 9 C ₂ H ₅ - CH ₃ O- 10 Cn) C ₄ H- CH ₃ O-- Ti ^ ⁰ : 1.5552 11 C I «CH« - CH ₃ O- 4 °: 1.5739 12th CH ₃ - C ₂ H ₅ O- n ^ °: 1.5635 13th CH ₃ - Cn) C ₄ H ₉ O- τξ °: 1.5550 14th CH ₃ - Ci) C ₄ H ₉ O- n £ °: 1.5536

609830/0928

link
No. ^R 5 6th H Physical
data 15th CH ₃ - (Se-Jc) C ₄ H ₉ O- Cn) CE ^ -
Ό iJ n ^ °: 1.5561 16 (H) C ₄ H ₉ - Cn) C ₄ H ₉ O- H n ^ °: 1.5406 17th CHo ^ CH ₀ ) oCH — CHrj "* H n ^ °: 1.5531 18th ^ CH ₂ - H n ^ °: 1.5875 19th CHg- CH ₀ OCH ₂ CH ₂ O- M.p .: 57-59 ° C 20th CHg- (n) C ₈ H ₁₇ O- n ^ °: 1.5386 21 CHg- (H) C ₁₀ H ₂₁ O- n ^ °: 1.5350 22nd CH ₃ - 0 - O- n ^ °: 1.5658 23 CH ₃ - n ^ °: 1.5925 24 M.p .: 44-47 ° C 25th CH ₃ - n ^ °: 1.5480 26th Θ " n ^ °: 1.5849

609830/0928

> N = CH - N

CH,

S -

(Ib)

COR,

link
No. ^R 5 ^R 6 Physical
data 27 CH ₃ - H n ^ °: 1.5879 28 C ₂ H ₅ - H ti ^ °: 1.5764 29 Cn) C ₃ H ₇ - H n ^ °: 1.5653 30th (X) C ₃ H ₇ - H n ^ °: 1.5679 31 (i) C ₄ H ₉ - H n ^ °: 1.5539 32 CH ₃ - CH ₃ - n £ °: 1.5800 33 CH ₃ - CH ₃ O- r ^ °: 1.5639 34 C ₂ H ₅ - CH ₃ O- n ^ °: 1.5559 35 Cn) C ₄ H ₉ - CH ₃ O- n ^ °: 1.5460 36 ClGH ₂ CH ₂ - CH ₃ O- n ^: 1.5644 37 CH ₃ - C ₂ H ₅ O- n ^ ⁰ : 1.5537

60 9830/092 8

link
No. ^R 5 ^R 6 K PhyS icaIi s che
data 38 CH ₃ - Cn) C ₄ H ₉ O- n ^ °: 1.5420 39 CH ₃ - (DC ₄ H ₉ O- r ^ °: 1.5414 40 CH ₃ - (sec.) C ₄ H ₉ O- n ^ °: 1.5451 41 Cn) C ₄ H ₉ - (n) C ₄ H ₉ O- nj °: 1.5270 42 CH ₃ OCH ₂ CH ₂ - H n ^ °: 1.5640 43 CH ₃ (CH ₂ ) ₃ CH-CH ₂ -
C ₂ H ₅ H n ^ °: 1.5415 44 D ^ CH ₂ - H r ^ °: 1.5728 45 CH ₃ - CH ₃ OCH ₂ CH ₂ O- n ^ °: 1.5509 46 CH ₃ - Cn) C ₈ H ₁₇ O- n ^ °: 1.5270 47 CHo ~ (U) C ₁₀ H ₂₁ O- νξ °: 1.5263. 48 CH ₃ - n ^ °: 1.5522 49 CH ₃ - n ^ °: 1.5776 50 l H t ^ °: I, 5öü9 51 CH ₃ - (H) C ₆ H ₁₃ - n ^ °: 1.5362 52 (Ty
1 N / 20th
n _D : 1.5749

6 0 9 8 30/0928

X-N = CH-N

S - N

- ^R

COR,

(Ic)

Verb.
No. 2-CH ₃ -4-Br-phenyl ^R 4 ^R 5 ^R 6 Physical
data 53 2-CH ₃ -4-Br-phenyl CH ₃ - ^C 2 ^H 5- H n £ °: 1.6042 54 2-CH ₃ -4-Br-phenyl- CH ₃ - CH ₃ - CH ₃ - n ^ ⁰ : 1.6073 55 2-CH ₃ -4-Br-phenyl- CH ₃ - C ₂ H ₅ - CH ₃ O- r ^ ⁰ : 1.5811 56 2,5-di-CH ₃ -4-Br-phenyl- CH ₃ - CH ₃ - C ₂ H ₅ O- ti ^ ⁰ : 1.5804 57 2-CH ₃ -3-Cl-phenyl CH ₃ - CH ₃ - H n ^ ⁰ ; 1.6130 58 2-CH ₃ -6-Cl-phenyl- CH ₃ - CH ₃ - H 5.9 2-CH ₃ -4-Cl-phenyl- CH ₃ - CH ₃ - C ₄ H ₉ O- i ^ °: 1.5449 60 3,5-bis-CF ₃ -phenyl- ^C 4S9 " CH ₃ - H n ^ °: 1.5780 61 4-NO _? -Phenyl- CH ₃ - CH ₃ - H M.p.: 50-51 ° C 62 2,3-di-Cl-phenyl- CH ₃ - CH ₃ - H M.p .: 85-87 ° C 63 2,3-di-Cl-phenyl- CHo - CH ₃ - H M.p .: 87-90 ^ C 64 2,4,5-tri-Cl-phenyl- CH ₃ - CH ₃ - CH ₃ O- n ^ °: 1.5841 65 CH ₃ - CH ₃ - H M.p .: 10 3-IO40C

609830/0928

co Ki co

link
No. X ^R 4 ^R 5 ^R 6 Physical data 66 2,4,5-tri-Cl-phenyl- CHg- CHg- CHgO- M.p .: 68-72OC 67 2,4,5-tri-Cl-phenyl- CHg- ClCH ₂ CH ₂ - CHgO- n ^ ⁰ : 1.5915 68 2,4,5-tri-Cl-phenyl- CHg- CHg- C ₂ H ₅ O- M.p .: 55-57 ° C 69 2,4,5-tri-Cl-phenyl- CHg- CHg- (I) C ₄ H ₉ O- n ^ ⁰ : 1.5738 70 2,4-di-Cl-phenyl- CHg- CHg- H n ^ ⁰ : 1.6143 71 2,6-di-Cl-phenyl- CHg- CHg- ' H 72 2,6-di-Cl-phenyl- CHo- CHg- CHgO- n ^ ⁰ : 1.5809 73 2-Cl-phenyl- CHg- CHg- H . n ^ ⁰ : 1.6135 74 3,5-di-Cl-phenyl- CHn - CHg- H n ^ °: 1.6183 75 3,5-di-Cl-phenyl- CHg- CHg- CHgO- n ^ ⁰ : 1.5923 76 3,5-di-Cl-phenyl- CHg- CH, - Cn) C ₄ H ₉ O- n ^ ⁰ : 1.5655

CO OO CO

link
No. ■ X ^R 4 H H Physical data 77 3,5-di-Cl-phenyl- CH ₃ - CH ₃ - (DC ₄ H ₉ O- n ^: 1.5653 78 2,6-di-C ₂ H ₅ -phenyl- CH ₃ - CICH /, οΗλ - CH ₃ O- n ^ °: 1.5492 79 2,6-di-G ₂ H ₅ ~ phenyl- CH ₃ - WC ₄ H ₉ - CH ₃ O- n ^ °: 1.5309 80 2 -CH ₃ -4-.Br-Pheny 1- CH ₃ - CH ₃ OCH ₂ CH ₂ - H n ^ °: 1.5934 81 3,5-bis-CFo-phenyl- CH ₃ - D " ^cv ■ H n ^ °: 1.5083 82 3,5-di-Cl-phenyl- CH ₃ - CH ₃ OCH ₂ CH ₂ - H νξ °: 1.5934 83 2,4,5-tri-Cl-phenyl- CH ₃ - CH ₃ - <^ Hy 0- M.p .: 57-61 ° C 84
, 1 4-NO ₂ -phenyl- .. ^C V Y- H M.p .: 67-70 ° C

CD-CD (JD OD -4

Example 2 Acaricidal Effect

Phaseolus vulgaris (plants) were tested for acaricidal action with an infected piece of leaf 12 hours before the test from a mass breed of Tetranychus urticae. proven. The defected moving stages were obtained from a chromatography nebulizer with the emulsified test preparations at a A concentration of 400 ppm dusted so that no runoff of the spray liquor occurred. After two and seven days, larvae Evaluated adults and eggs under the dissecting microscope for living and dead individuals.

During the holding time ¹¹ , the treated plants stood in greenhouse cabins at 25 ° C. In the above test, the compounds according to Example 1 were effective against adults, larvae and eggs of Tetranychus urticae. Because of their particularly good action, compounds 1-23, 25, 28, 30, 33, 35, 36, 37-44, 46-49, 51 and 56 are highlighted.

Example 3

Action against ticks A) Rhipicephalus bursa

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

609830/0928

• η-

The evaluation was carried out after 2 weeks for the adults and after 2 days for the larvae. Run for every attempt 2 repetitions.

B) Boophilus microplus (larvae)

With an analogous dilution series as in test A, 20 sensitive resp. OP-resistant larval trials carried out. (The resistance refers to the tolerance of Diazinon).

In these tests, the compounds according to Example 1 were effective against adults and larvae of Rhipicephalus bursa and against sensitive ones resp. OP-resistant larvae of Boophilus microplus.

Example 4

Broad beans (Vieia faba) grown in pots were used with infected the test insect Mjfous persicae), whereby the average infection was approximately 200 individuals per plant.

The application of the test substance (obtained 0 ₃ 17 _o acid aqueous emulsion of an emulsifiable concentrate _o L07) carried out 24 hours after the settlement by means of compressed air from syringe 30 cm distance with the spray jet to the aphids occupied sheets.

Two plants were used per test substance. The experiment was carried out at a temperature of 24 ° C and 60% relative air

0 9 8 3 0/0928

moisture carried out.

Compounds 2, 6, 10, 12, 13, 15, 17-19, 25, 33-35, 37, 38, 40, 42-45, 50-52, 59 and 79 according to Example 1 showed im Above attempt a good effect against Myzus persicae.

Example 5

In plastic dishes with a soil / peat / sand mixture were placed Sown seeds of the grasses Lolium perenne, Zoa pratensis, Festuca ovina and Dactylis gjomerata. After three weeks the emerged grasses were up to 4 cm above the Cut back the soil and sprayed with an aqueous spray mixture of the active ingredient 2 days later. The amount of active ingredient was converted kg of active ingredient per hectare. 14 days

after the application, the grass was growing

evaluated.

Compounds of the formula I showed a in the above experiment

good inhibiting effect.

609830/0928

Claims (12)

Expectations (D COR ₆ R ₁ , R ₉ and Ro independently of one another a hydrogen or halogen atom or a C -, - C, -alkyl-, C ₁ -C ₄ -AIkOXy-, C ₁ -C, -alkylthio-, trifluromethyl-, cyano- or Nitro group R, a C ₁ -C, -alkyl group, R _{5 is} an optionally halogen-substituted C ₁ -C ₁ -alky group or a Co-C ₁₀ -Cycloalkyl, C _{1 -C 10} (cycloalkylalkyl) or Cp-C ₁₀ - (alkoxyalkyl) group, and R, a hydrogen atom; an optionally halogen-substituted C ₁ -C 4 -alkyl or C ₁ -C 4 -alkoxy group; or a Cq-C ₁ ^ .- cycloalkyl, Co-C _1n -CyClOaICyIoXy-, C ₇ -C _1n - (CyClOaICyI-alkyl) -, C ₄ -C ₁₀ - (cycloalkyalkoxy) -, C ₂ -C ₁ - (AlkoxyaIky1) - or Cp ^ C ₁₀ - (alkoxyalkoxy) group. 2. Compounds according to claim 1, wherein R _{1 is} a C ₁ -C ₄ -A ^ y! Group in the place ho-S division, R _{2 is} a C - ^ - C ^ alkyl group or a halogen atom in the para Position, Ro is a hydrogen atom and R _{4 is} a methyl group. 609830/0928 3. Compounds according to claim 2, wherein R, a methyl group in the ortho position, R "is a methyl group or a chlorine or bromine atom in the Para position mean. 4. Compounds according to claim 1, wherein R, a C-, -C, -alkyl group in the Ortho-S te llung, R2 a C ₁ -C, -alkyl group or a halogen atom in the Para position,
R "a hydrogen atom, R, represents a methyl group and either i) Rc is an optionally halogen-substituted C.-C .-- alkylene group or a C, -C _1n cycloalkyl, C, -C!. Represents (cycloalkylalkyl) or C ^ -C, _o - (alkoxyalkyl) group, while R 1 represents a hydrogen atom, or ii) Rc represents an optionally halogen-substituted C _{1 -C 1n} -alkyl group, while R ₆ for an optionally halogen-substituted C.-C .. ,, - alkyl or C ₁ -C _1n -alkoxy group or a Cj-C .. cycloalkyl ", C ₃ -C ₁ -CyClOaIkOXy-, C, -Cj- (Cycloalkyla Hey1), C 1 -C ₁₀ (cycloalkylaIkoxy), C _{1 -C 10} "(alkoxyalkyl) or C ₉ -C 1 (alkoxyalkoxy) group. 609830/0 92 β 5. Compounds according to claim 4, wherein R- is a methyl group in the ortho position, R is a methyl group or a chlorine or bromine atom in the Para-position and either i) R _{5 is} a C ^ -C ^ alkyl, C ₃ -C ₆ -CyCloakyl-, C ^ C ^ cycloalkyl, C - C «-alkyl or C - C, -alkoxy-C ..-C, -alkyl group represents while R ^ represents a hydrogen atom, or ο ii) Rc represents an optionally halogen-substituted C, -C -alkyl group, while
R. for a C _n -C ₁ , - alkyl-, C _n -C _1n -AIkOXy-, C ~ -C, -Cyclo- O 1 IU J- J-U J D alkyl-, C ₃ -C ₆ -CyClOaIkOXy-, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₂ - Alkyl -, C ₃ -C -CyClOaIk ^ lC ₁ -C ₂ -alkoxy-, C ₁ -C ₄ -AIkOXy- _c _ _c CT ^ alkyl or C ^ alkoxy-CT ^ -C alkoxy group. 6. l, 3,5-Triaza-4-sulfa-l- (2-methyl-4-chlorophenyl) -3-methyl-5-acetyl-hexen-(1), according to claim 1. 7. l, 3,5-Triaza-4-sulfa-l- (2-methyl-4-chlorophenyl) -3-methyl-5-formyl-7-methoxy-hepten- (l) according to claim 1. 8. 1,3,5-Triaza-4-sulfa-1- (2-methyl-4-chlorophenyl) -3-methy1-5-formyl-hepten- (l) according to claim 1. 9. Process for the preparation of compounds of the formula I according to claim 1, characterized in that one Compound of formula II 609830/0928 (H) in the presence of a base with a compound of the formula III Hal-SN ' (III) converts, where in the formulas II and IHR ₁ to R the im l ο Claim 1 have already given meanings and "Hai" represents a halogen atom. 10. Agents for combating pests, characterized in that that it contains a compound of the formula I according to claim 1 as active ingredient. 11. Methods of combating insects and / or representatives of the order Akarina, characterized by the use of a compound of the formula I according to claim 1. 12. Use of a compound according to claim 1 for influencing of plant growth. 609830/0 928