DE2129678A1 - Herbicides and pesticides - Google Patents

Description

"Herbicides and pesticides"

The invention relates to SuIfoxirainderivate, the herbicidal and have pesticidal properties.

In particular, the invention relates to a carrier or surfactant biologically active agent or both a carrier and a surface active agent together with at least one sulfoximine derivative of the general Formula:

NO,

in which R- is an optionally substituted aryl group, R "is a

109853/1975

Alkyl or aryl group or IL and Hp together are a polymethylene group and H ^ represent a hydrogen or halogen atom or a nitro or acyl group, or salts thereof Compounds as an active ingredient. Examples of suitable substituents on the aryl group are halogen atoms, hydroxy, nitro, Alkyl, alkylamino and dialkylamino groups and dialkyl phosphorothionate groups.

In the following, “acyl group” is understood in the broadest sense to mean a group which is characterized by. Removal of a hydroxyl group has been obtained from an organic acid and not P exclusively includes groups derived from carboxylic acids and their thio analogs, such as alkaneyl groups and substituted carbamoyl groups, but also groups derived from substituted carboxylic acids and thiocarboxylic acids, e.g. Alkoxycarbonyl and alkylthiocarbonyl groups, or those derived from organic sulfur _$ example, an alkyl or arylsulfonyl group.

Preferred agents according to the invention are those in which the active ingredient is a sulfoximine derivative of the formula I, where ü. represents a phenyl group, optionally with one or more halogen atoms, e.g. chlorine, bromine or iodine atoms or by one or more nitro groups or a hydroxy or alkyl group, such as a methyl group or alkylamino group, e.g. the propylamino group, a dialkylamino group, e.g. the dipropylamino group or Dialkyl phosphorothionate group, e.g. diethyl phosphorothionate group, is substituted, E _{2 is} an alkyl group with 1 to 6 carbon atoms, e.g. the methyl or a phenyl group or It. And Rp together represent a polymethylene group with up to 5 carbon atoms, e.g. the tetramethylene group and S _{7 is} hydrogen - or chlorine atom, an optionally chlorinated alkanoyl group with 1 to 6 carbon atoms, in particular a formyl, acetyl, chloroacetyl,

• _ 3 «.

109853/1975

Dichloroacetyl, propionyl, dichloropropionyl, butyryl or ibobutyryl group, a cycloalkylcarbonyl group, in particular a cyclopropylcarbonyl group, an aroyl group, especially a benzoyl group, an N-substituted or Ν, Ν-disubstituted carbamoyl group, especially one Methylcarbamoyl, ethylcarbamoyl, phenylcarbamoyl, chlorophenylcarbamoyl, Dichlorophenylcarbamoyl-, tolylcarbamoyl- or dimethylcarbamoyl group, an alkoxycarbonyl group, in particular an ethoxycarbonyl group, an aralkoxycarbonyl group, especially a benzyloxycarbonyl group, an (alkylthio) carbonyl group, especially the (ethylthio) carbonyl group or an alkyl, aryl or alkarylsulfonyl group, 25.B. a methylsulfonyl, phenylsulfonyl or tosyl group or a sulfate or alkaryl sulfonate, e.g., toluene sulfonate such a connection means.

Particularly preferred agents are those that have the compound as the active ingredient

S- (3,5-Dinitro-4-N ', N'-dipropylaminophenyl) -S-methylsulfox-

imine included.

The majority of the compounds that are used in the agents according to the invention are new compounds. The invention therefore also encompasses new sulfoximine derivatives of the formula I in which E., R "and R" have the stated meaning with the proviso that when R ^ and R "are each a phenyl group or together are a tetramethylene group or R _{1 is} a phenyl group which is substituted in the 4-position by a chlorine atom or a nitro or methyl group and R _{2 represents} a methyl group, R 1 does not represent a hydrogen atom.

Preferred and particularly preferred sulfoximine derivatives with the above stipulation are those above as active

109853/1975

Components of the preferred and particularly preferred herbicidal and pesticidal agents have been mentioned.

The invention also relates to "methods of manufacture of the new sulfoximine derivatives. Compounds of formula I, where R, denotes a hydrogen atom, are by reacting of a sulfoxide of the formula:

so

with hydrazoic acid _{s s} can be produced advantageously in situ by the action of an acid, such as sulfuric acid to an alkali metal azide such as sodium azide prepared. The reaction can be carried out in an organic solvent such as chloroform.

Those compounds in whose formula IR ^ is an acyl ^; group means, can generally be obtained that a compound of formula I, in which R ^ is a hydrogen atom, with an acyl halide, advantageously an acyl chloride, preferably in the presence of an acceptor for hydrogen halide, for example, a tertiary alkyn such as triethylamine or pyridine. The reaction can, if appropriate, be carried out in an inert organic solvent, for example _{0, ether.}

Other methods may be used in certain cases, polygamy sometimes preferable as the more convenient method are. Those compounds in whose formula I R, denotes an alkanoyl group, can by reacting the ent-

- 5 109853/1975

speaking sulfoximine with an acid anhydride, expedient in the presence of the corresponding acid. Those compounds in whose formula I R ^ a means mono-N-substituted carbamoyl group can be obtained by reacting the sulfoximine with an organic isocyanate getting produced.

Those compounds in whose formula I R is a halogen atom can be obtained by reacting the sulfoximine with a halogenating agent, e.g. elemental halogen or an alkali metal hypohalite such as sodium hypochlorite in acidic solution, preferably in aqueous acetic acid solution. The compounds, in whose formula IR, denotes a nitro group, can by Nitration of the sulfoximine using, for example, a mixture of nitric acid and sulfuric acid will.

In the following, “carrier” is understood to mean a material which is inorganic or organic or synthetic or may be of natural origin with which the active compound is mixed or formulated to make the application on plants, seeds, the soil or any other object to be treated or on storage, transport or to make handling easier. The carrier can be solid or a liquid. The usual for formulation Agents applied by herbicides and pesticides can be used as carriers.

Suitable solid supports are natural and synthetic clays and silicates, for example natural silicas such as Diatomaceous earth, magnesium silicates, e.g. talc types, magnesium aluminum silicates, e.g. attapulgites and vermiculites, Aluminum silicates, e.g. kaolinites, montmorillonites and mica, calcium carbonates, calcium sulfate, synthetic hydra-

- 6 - 109853/1975

tized silicon oxides and synthetic calcium or aluminum silicates, elements, e.g. carbon and sulfur, natural and synthetic resins, e.g. coumarone resins, polyvinyl chloride and styrene polymers and copolymers, solid polychlorophenols, bitumen, waxes, e.g. beeswax, Paraffin wax and chlorinated mineral waxes, as well as solid fertilizers e.g. superphosphates »

Suitable liquid carriers are water, alcohols, for example isopropanol and glycols, ketones, z "B _o acetone, methyl ethyl ketone, Hethylisob, utylketon and cyclohexanone, ethers, w aromatic see hydrocarbons such as benzene _s toluene and xylene, petroleum fractions such as kerosene, light mineral oils, chlorinated hydrocarbons such as carbon tetrachloride _s, perchlorethylene and trichloroethane and liquefied, normally vaporous and gaseous compounds. Mixtures of different liquids are often suitable.

The surfactant can be an emulsifier or a dispersant or a wetting agent. It can't be ionic or ionic «The surfactants commonly used in the formulation of herbicides or pesticides Funds can be used. Examples of suitable surface-active agents are sodium or Calcium salts of polyacrylic acids and lignosulfonic acids, the condensation products of fatty acids or aliphatic amines or amides with at least 12 carbon atoms in the Molecule with ethylene oxide and / or propylene oxide, fatty acid ester of glycerine, sorbitol ^ sucrose or pentaerythritol, ■ Condensates of these compounds with ethylene oxide and / or propylene oxide, condensation products of fatty alcohols or Alky! Phenols, e.g. p-octylphenol or p-octylcresol with Ethylene oxide and / or propylene oxide, sulfates or sulfonates of these condensation products, alkali or alkaline earth metal salts, preferably sodium salts of sulfuric acid esters or

- 7 -109853/1975

Sulfonic acid ester]! with at least 10 carbon atoms im Molecule, e.g. sodium lauryl sulfate, sodium sec.-alkyl sulfate, Sodium salts of sulfonated castor oil and sodium alkylarylsulfonates, such as sodium dodecylbenzenesulfonate, as well as polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The agents according to the invention can be used as wettable powders, dust preparations, granules, solutions, emulsifiable concentrates, Emulsions, concentrated suspensions and aerosols can be formulated. Wettable powders usually go like this compiled that they contain 25, 50 or 75 wt .-% active ingredient and usually in addition to the solid support 3 to 10% by weight a dispersant and, if necessary, 0 to 10 wt .-% stabilizers and / or other additives, such as Means to improve penetration or adhesion, contain. Dust preparations are usually made as a dust concentrate with a similar composition to that of wettable powders, but without dispersants, formulated and diluted in the field with another solid carrier, whereby an agent is obtained which usually contains 1/2 to 10% by weight of active ingredient. Granules usually become like this manufactured so that their size corresponds to a clear sieve mesh size of 1.6? 5 to 0.152 mm, the production takes place by agglomeration or impregnation processes.

In general, the granules contain 1/2 to 25% by weight Active ingredient and 0 to 10% by weight additives, such as stabilizers, agents for slowing down the release of active ingredients and binders. Emulsifiable concentrates usually contain, in addition to the solvent and, if necessary, cosolvents, 10 to 50% by weight active ingredient, 2 to 20% by weight Emulsifiers and 0 to 20% by weight of corresponding additives, such as stabilizers, agents for improving penetration and

- 8 1Q9853 / 1975

Corrosion inhibitors by volume. Econcentrated Suspensions are composed in such a way that a stable, non-sedimenting flowable product is obtained. They usually contain 10 to 75 wt .-% active ingredient, 0.5 to 15 wt .-% dispersant, 0.1 to 10% by weight of suspending agents, such as protective colloids and thixotropic agents, 0 to 10% by weight of corresponding additives, such as defoaming agents, corrosion inhibitors, stabilizers, Means for improving the penetration and adhesion as well as water or an organic liquid as a carrier, k in which the active ingredient is practically insoluble. Certain organic solids or inorganic salts can im Carrier to be dissolved to prevent sedimentation or as an antifreeze when using water.

The agents according to the invention can also contain other ingredients, e.g. other compounds with herbicidal, Pesticidal or fungicidal properties.

Aqueous dispersions and emulsions, e.g. agents obtained by diluting a wettable powder or a emulsifiable concentrate obtained according to the invention with water are also within the scope of the invention. These emulsions can be water-in-oil emulsions or oil-in-water emulsions and they can be a thick mayonnaise type Have appearance. -

A method is also within the scope of the invention to control weeds and / or insects and / or acarids in cultivated areas, which consists in that on the A biologically effective amount of an agent or a sulfoximine derivative according to the invention is applied to the cultivated area will. . ,

The invention is illustrated in more detail by the following examples,

- 9 -109853/1975

_ Q -

Example 1 S- (2-chloro-4-nitrophenyl) -S-methylsulfoxime i

11 g of 2-chloro-4-nitrophenyl methyl sulfoxide were dissolved in a mixture of 200 ml of dry chloroform and 20 ml of concentrated sulfuric acid. To the mixture, which was kept at 48 Ms 53 ° C. for 3 hours, 6.5 g of dry sodium azide were added. The mixture was stirred vigorously at this temperature for a further 24 hours and then poured into ice water. The chloroform layer was separated and the aqueous layer was neutralized with an aqueous sodium carbonate solution. The neutralized solution was extracted with chloroform and the combined chloroform solutions were dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The desired product with a melting point of 85 to 88 ^° C. was obtained.

Analysis;

For C ₇ H ₇ N ₂ SO ₅ Cl: C, 35.9; H 3.0; N 11.9%

Found: C, 36.2; H 2.9; N 11.9%

109853/1975

Example 2 S- (2-chloro-4-nitrophenyl) -S-methyl-N-acetylsulfoximine

There was added 1.5 g of S- (2 ~ chloro-4-nitrophenyl) -S-methylsulfoximin, which had been prepared as in Example 1 and 1 ml of acetic anhydride in 4 ml of glacial acetic acid for 1 hour at 5O ⁰ G heated. Water was added to the mixture and the solid substance obtained was filtered off, dried and recrystallized from a mixture of acetone and petroleum ether (boiling point 40 to 60 ° C.). It was the desired product from i ¹ . 161 to 163 ° C obtained.

Analysis:

Calculated for C ₉ H ₉ N ₂ SO ₄ Cl: C, 39.2; H 3.3; N 10.1; S 11.6%

Found: C, 39.7; H 3.3; N 10.3; S 11.6%

Example 3 S-methyl-S- (4-nitrophenyl) -N -chlorosulfoximine

1.0 g of S-methyl-S- (4-nitrophenyl) sulfoximine in 50 ml of dry chloroform was treated with gaseous chlorine under irradiation with a heating lamp for 2 hours. The mixture was filtered off and the solid substance obtained was made from a mixture of acetone and petroleum ether (b.p. 40 to 6O ⁰ G)

- 11 109853/1975

recrystallized. The desired product with a melting point of 158 to 160 ^° C. was obtained.

Analysis;

For C ₇ H ₇ N ₂ SO ₅ Cl: C, 35.9; H 3.0; N 12.0; S 13.7 %

Found: C, 35.7; H 3.7; N 11.7; S 13.4-%

Example 4

S-methyl-S- (4-nitrophenyl) -N- (N ', N'-dimethylcarbamoyl) -sulfoximine

There were 0.75 g of S-methyl-S- (4-nitrophenyl) sulfoximine and 0.4 g of dimethylcarbamoyl chloride in 40 ml of dry pyridine Heated under reflux for 6 h. The solution was evaporated to dryness under reduced pressure. The residue was with Treated dilute hydrochloric acid and extracted with benzene. The benzene extracts were dried and reduced under reduced pressure Pressure evaporated to dryness. The desired product with a melting point of 135 ° to 137 ° C. was obtained.

Analysis:

Calculated for C ₁₀ H ₁₃ N ₃ SO ₄ : C, 44.4; H 4.8; S 11.8%

Found: C, 44.3; H 4.7; S 12.4%

Example 5 S-methyl-S- (4-nitrophenyl) -N- (N'-phenylcarbamoyl) sulfoximine

There were 1.0 g of S-methyl-S- (4-nitrophenyl) sulfoximine and 0.6 g of phenyl isocyanate in a mixture of toluene and petroleum ether (b.p. 60 to 8O ⁰ C.) Of 2: 1 4 1/2 h at reflux heated. The solution was filtered and evaporated to dryness under reduced pressure. The residue was stirred with a hot mixture of Aceton'und petroleum ether (bp. 60 to 80 ⁰ C). It found the desired product to be crystalline

- 12 109853/1975

Substance obtained from P. 148 to 150 ° C.

Analysis:

Calculated for C ₁₄ H ₁₅ N ₅ SO ₄ : Q 52.7; H 4 ", 1; N 15.3%

Found: 'C 53.0; H 4.2; N 13.0 %

Example 6 S- (4-chlorophenyl) -S-methyl-N-etiioxycarbonylsulfoximine

0.76 g of S- (4-chlorophenyl) -S-methylsulfoximine, 0.43 S of ethyl chloroformate and 0.4 g of triethylamine in 40 ml of ether were refluxed for 6 1/2 hours. The mixture was filtered and evaporated to dryness under reduced pressure. The desired product with a melting point of 70 to 73 ° C. was obtained.

Analysis:

For C ₁₀ H ₁₂ NSO ₃ Cl: C, 45.9; H 4.6; N 5.4%

Found: C, 45.9; H 4.8; N 5.2%

Example 7

Nitration of S- (4-chlorophenyl) -S-methylsulfoximine

1.0 g of S- (4-chlorophenyl) -S-methylsulfoximine was treated dropwise with 3 ml of fuming sulfuric acid and then with 1 ml of fuming nitric acid at 5 "to 15 ° C. The mixture was stirred at 30 to 35 ° C. for 6 h and then poured into a solution of sodium hydroxide in ice. After vigorous stirring, a white precipitate was obtained, which was filtered, dried and recrystallized from a mixture of acetone and petroleum ether (b.p. .. 40 to 6O ⁰ C). It has been S- ( 4-chloro-3-nitro, rophenyl) -S-methyl-N-nitrosulfoximine obtained as a colorless crystalline substance with a melting point of 164 to 168 ° C.

- 13 -

109 853/1975

Analysis; Calculated for C ₇ H ₆ N ₃ SO ₅ Cl Found

C 30.1; H 2.2; N 15.0; S 11.5% C 30.4; H 2.0; N 14.8; S 11.6%

The aqueous alkaline solution was acidified and extracted with chloroform. The extracts were dried and evaporated to dryness under reduced pressure. There was obtained a crude which gave after recrystallization from benzene S- (4-chloro-3-nitrophenyl) -S-methylsulfoximin, mp 118-120 ⁰ C.

Analysis: calculate

Found

Calculated for C ₇ H ₇ N ₂ SO ₅ Cl

C 35.8; H 3.0; N 11.9% C 36.1; H 3.0; N 11.3%

example S- (4 ~ chlorophenyl) -S-methyl-N-tosylsulfoximine

1.89 g of S- (4-chlorophenyl) -S-methylsulfoximine were obtained and 1.90 g of p-toluenesulfonyl chloride in 10 ml of pyridine for 3 hours heated to 100 ° C. Water was added to the cooled solution, a crude product precipitating which after recrystallization from ethanol gave the desired product with a melting point of 125 to 127 ° C. '

Analysis: Calculated for

Found example

C48.9, H4.1, N4.1% C 48.9; H 4.0; N 3.7%

Similar to the procedures mentioned, further compounds were made

whose physical properties and analytical values are given in Table I below.

- I4 -

109853/1975

TABLE I.

link

F. ⁰ C

analysis

S- (4-chloro-pheny l) -S-me thy 1-N-ace ty 1-
sulf oximin 75-80 Ber.
Found for C ₉ H ₁₀ NSO ₂ Cl: C.
C. 46.7
46 '. 6th ; η
; η 4.4;
4.4 y N
N 6.0%
5.8% S.
S. 13 ^ 2%
13.1% SM "ethyl-S- (4-nitrophenyl ') - N-acetyl-
sul foximin 119-121 Ber.
Found for ViOV ⁰ A; C.
■ c 45.7
45.3 ; η
; η 4.1!
4.3 N
N 11.6;
11.5; co
OO
cn S- (4-Cfa; Lor- ~ 2-nitrophenyl) -S-methyl-
sul ■ £ oximin 114-116 Ber.
Found for C ₇ H ₇ N ₂ SO ₃ Cl: C.
C. 35.9
36.1 ; η.
; η 3.0
2.9 i 2 11.9%
10.5% I. <o S- (3,5-f) initro-4 ~ N, N -dipropylaminophenyl) -
S-methylsul-f o> ximin ' 85-88 Ber ο
Found for ^C 13 ^H 2O ^N 4 ^SO 5; C.
C. 45.4
45.1 ; η
; H 5 ^f , 9 16.3%
16.3% cn S-methyl-S- (2-nitrophenyl) sul-oximine 94-96 Ber.
Found for C ₇ H ₈ N ₂ SO ₃ : C
i C 42 ₇ 1
42.4 ; η
; η 4.0
4.3 ; ν
; N 14 ^ 0%
13.6% SK-ethyl-S- (4-nitrophenyl) -N- (N'-methyl
carbamoyl) sulf .oximin " 131-133 Ber.
Found for C ₉ H _n N ₃ SO ₄ : C
: C 42 _? O
41.7 ; η
; η 4.3%
4.3% S.
S. 9.0%
9.2% S-methyl-S- (4-nitrophenyl) -N- (N '- (3-
chlorophenyl) carbamoyl) su] f oximin 154-156 Ber.
Found for ■ ^C 14 ^H 12 ^N 3 ^SO 4 ^C1 ; I. 47.5
47.4 ; η
; η 3.4
3.4 ; ν
; ν 11.9;
11.6; S.
S. 9.0%
9.3% S- (2- chloro-4-nitropheny I) -S-XQe thy 1-
N- (H'-phenylcarbamoyl) suI foximin 219-222 Ber.
Found for ^C 14 ^H 12 ^N 3 ^SO 4 ^C1 : I. 47.5
49.4 ; η
; η 3.4
3.8 ; ν
i " 11.9;
11.4; I.

Continued TABLE I:

2129578

Cont'd, to TABLE

link

τ?

Yy

analysis

S- (2-G-.lor -4-nitrophcnyl) -S-mathyl-N- (N ^T -
(3-chloro-phenyl) carbsmoyl) sul f oxinin 168-170 Ber. for C ₁₄ H _n N ₃ SO ₄ Cl ₂ :
ιίθχ. ' C 43.3; H 2.8; N 10.8%
C 43.5; H 3.0; N 10.6% S- (4-chloro-phenyl) -S-n2thyl-N- (N'-
phenylcarbamoyl ') sulf oximiti 149-151 Ber. for C ₁ .H. , N.SO ₀ Cl:
Γλ-f 14 13 2 2 C 54.4; H 4.2; N 9.1%
C 54, '6; H 4.3; N 9.0% __ *
O
CO
CO
err
UJ S- ^(4-c nlor-phenyl) -S-methyl-K- (N ^t -
(3-chloro-phenyl) carbanoyl) sulf.oximine 131-134 Ber. for c ,, H ₁₀ N.so_cl ":
Found 14 12 2 2 2. C 49.0; H 3.5; N 8.2; S 9.3%
C 48.7; H 3.4; N 8.3; S 9.5% —Jk
tx>
-J
cn SW ₂ ethyl-S- £ -toIv 1-N- (N '- (3,4-dichlorophenyI) -
carbasoyl) sul f oxitain ' 182-184 Ber. for C ₁ -H ₁ -N ₉ SO ₀ Cl ₉ ■
Found 15 14 2 2 2. C 50.5; H 3.9; N 7.8% '
C 50.3; H 4.1; N 7.8% SM ethyl-S- (4-nitrophenyI) -N- (N * - (3,4-
dichloropheny Dcarbanoyl) sul f oximin 127-129 Ber. for C ₁ -H ₁₁ N-SO-Cl.
Found ^{uu 3 4 2} C 43.3; H 2.8; N 10 _; 8% ^
C 44.6; H 3.0; N 10.6% ς « S- (4-C.hlor-phenyi) -S-taethyl-N - ((ethylth £ o) -
carbonyl) -sul-f .oximin 88-90 Ber. for C _1n H ₁₀ NS ₀ O ₀ Cl
Found ^{10 12 2 2} C 43.2; H 4.3; N 5.0%
: C, 43.6; H 4.6; N 5.0% S - ^. Ethyl-S- (4-nitrophenyl) -N- (N'-
a. ethylcarbamoy 1) sulf iOximin 105-107 Ber. for ^C _1O ^H ₁₃ ^N 3 ^SO ₄
Found. : C, 44.3; H 4.8; N 15.5%
: C, 44.3; H 5.0; N 15.2% S- (4-Ctllor-3-nitrophenyl) -Sn: ethyl-N- (N * -
rcetnylcarbaffioyl) suri 'oximin 169-171 Ber. for CHN so Cl
Found ^{y 4} : C 37.1; H 3.4; N 14.4; S 11.0%
: C 39 _; 1 ; H 3.6; N 13.6; S 10.6% SiSiDiphenyl-N- (N * -methylcarbamoyl) sul £ .oximin 183-185 TeV. ^{for 0} U ¹ UV ⁰ I. : C, 61.4; H 5.2; N 10.2%
: C, 61.5; H 5.1; N 11.6% S- (3,5- DLnitro-4-propylamxnophenyl) -
S-nathylsulfoximin
I. 160-162 Ber. for C ₁₀ H ₁₄ N ₄ SO ₅
vjr Θ Χ · : C 39.8; H 4.6; N 18.6; S 10.6%
: C, 40.1; H 4.7; N 18.1; S 10.5Z

Continued TABLE I _:

Ports, to TABLE I.

link P. ⁰ C Ber.
Found for analysis C 46.6;
C 46.4; H 5.7
H 5.8 > 4th
4th N
N » 14.5%
14 _; 2% 12th
13th ψ S- (3,5-Plnicro-4-NiN ^l -dipropyIaaiinophenyl) -
-S-r.athyl-N-acetylful · ^ oxitsin 160-162 Ber.
Found for ^C 15 ^H 22 ^N 4 ^S ° 6; C 39.8;
C 40.0; H 5.2
H 5 ₇ 5 j 9
0 N
N *
> 13 _; 3Z
13 j IZ I. S- (3,5-0 i.nitro-4-Κ JK'-dipropylaainophenyl) -
■ "S-usthy 1 — K-cathati— ■ sulphonyl sulfoximine 189-191 Ber.
Found for C ₁₄ H ₂₂ N ₄ S ₂ O ₇ : C 48.1;
C 47 ^ 8; H -5.3
H 5 ₇ 5 » 9
1 N
N »
*
* 11.2%
11/2% S 7
S 7 S- (3,5-nitro-4-NlN'-dipropylaminophenyl> -
-S-Esthyl-N-to $ yl * ul; -f oximin 182-184 Ber.
Found for ^C 2O ^H 26 ^N 4 ^S 2 ° 7; C 51.8 ;
C 51 _; 4, H 5 _; 4th
H 5 _; 5 >
» 2
1 N
N ; 15, IZ S.
S. CD S- (3,5-Dinitro-4-NJN * -dipropylaainopheeyl) -
-S- ^ ethyl-N-CN'-phenylcerbsmoyDeulf oximin 194-195 Ber.
Found for ^C 2O ^H 25 ^N 5 ^SO 6. C 57 _; 2
C 57 _; 1 , ; H 6.4
H 6.3 >
» N
N 11.1%
10 ^ 8% CO
CD
cn
to S, S-Tetrafathy IeO-TN- (K ¹ -m-tolylcarbaiQoyl) -
sulf oximin 128-130 Ber.
Found for ^C 12 ^H 16 ^N 2 ^S0 2 C 56.9
C 57.3 ; H 6.0
; H 6 _; 2 * N
N 5.5; S.
5.4; S. / 19th S, S-Ietranethylea -W- (beazyloxyc * rbonyl) -
sul-f oxinine 80-82 Ber.
Found for C ₁₂ H ₁₅ NSO ₃ C 45 _r 0
C 45 _r l ; H 5.8
; η 5.8 N
N 17.5Z S.
S. 7 ™
, 1Z tn S- (3,5-ainir.ro-4-N ^f , N ^f -diptopyl «binophenyl) -
-S-nethyl-N- (li ^l -iaethylc4irbaiBoyl) eul f oximia 145-147 Ber.
Found for ^C 15 ^H 23 ^N 5 ^S0 6 C 42.8
C 42.9 ; η 5.0
; H 5.1 N
N 13.3;
τ * y Q ι- - S- (3,5- | Hnitro-4-NiNWipropyl * minophenyl) -
. -S-ethyl-N-chlojJ-'acetylsulf-oximine 180-182 Ber.
Found for : C 39 _T 6
: C 39.9 ; η 4,
; H 4, N 12.3;
N 12.2; > ⁶ *.
-8Z S-C3.5-D initro-A-NiK'-dipropylJBoinophenyl) -
—S — ins thy 1 — Ν — dixhloi ^ ecctylsulf oxiroim 213-215 Ber.
Found for : C 36.8
: C 37.2 ; H 3,
; η u, N 11.4Z
N11,2Z 7.0Z oftthyl-N-trichioroacetyleul f oximin ·. 236-237 Ber.
Found for C 49.4
C 49.2 ; η 5,
; η 6, N 13 _? 6Z
N 13.2Z S-O.S-tlinitro-A-SjN'-dipropylaminophenyD-S-
oethyl-N-cyclopropyicJirtonylsulfoximin 184-186 Ber.
Found for C 53.2
C 53.1 ; η 6 _r
; η 6, N 12.4;
N 12.0; I cul f oximin 95-98 ELLEoT 14, 2Z
14.0Z ^C 15 ^H 21 ^N 4 ^SO 6 ^C1 ; ^C 15 ^H 2O ^N 4 ^SO 6 ^CX 2 ^C 15 ^H 19 ^N 4 ^SO 6 ^C1 3 ^C 17 ^E 24 ^N 4 ^SO 6 j ^C 10 ^H 14 ^N 2 ^S0 2 J. ij'orts. ^x > do:

link

Ports, to P- ⁰ C

TABEL

analysis

S- (3,5-D initro-4-NJN'-dioropy1aminophenyI) -S-
cathy1-Np rop i cny1s ulf oximin 173-175 Ber.
Found for ^C 16 ^H 24 ^N 4 ^S0 6 47 ;8th "H
; η 6 ^ 2 ; ν
i ν 13; 6% ; s
, s 6.8%
7.2% S- (3,5-Dinitro-4-N ^ '- dipropylaainophenyl) -S-
Ethyl-N-2,2-dichloropropionyl sulfoxirain 235-237 Ber.
Found for ^C 16 ^H 22 ^N 4 ^S0 6 ^C1 : to ; t ; η
; η 4.7
V ; ν
; ν 11.9
11.8 S- (3,5-ß initro-4-NiN ¹ -dipropylaminophenyl) -S-
ethyl-N-butyrylsul-oxinine 163-165 Ber.
Found for ^C 17 ^H 26 ^N 4 ^S0 6 49
48 , 9 ; η
; η 6.3
⁶ I ⁵ ; N
; ν 13.5%
13.3% S- (3,5-1) initro-4-Ν ', - Ν' -dipropylaninophenyI) -S-
ethyl-N-isobutyrylsulfoximine 206-209 Ber.
Found for ^C 17 ^K 26 ^K 4 ^S0 6 49
49 ? 3 ; η
; η 6.3
6.3 ; N
; N 13.5%
13.2% S- (3,5-Dinitro-4-N; N'-dipropylaziinophenyl) -S-
Ethyl-N-benzoyl sulfoximine 148-150 Ber.
Found for ^C 2O ^H 24 ^N 4 ^SO 6 53 U ; η
; η 5 ₇ 4 ; ν
; ν 12.5%
12.4% « S- (3,5-Dinitro-4-N * -propylaminophenyl) -S-
rsethyi-N-acetyl sulfoximin 102-104 Ber.
Found for ^C 12 ^H 16 ^N 4 ^SO 6 ' 41
42 , 9
r3 ; η
; η V
4.8 ; ν
; ν 16.3%
16 _; 1% S '
s: 19.7%
L8.9% - S- (4-fi y droxyphenyl) -S-nethyl-N-tosy 1-
sulf oximin 186-188 Ber.
Found for ^C 14 ^H 15 ^NS 2 ° 4 51
51 , 7
r8 ; η
; η 4.7
4.8 ; N
; N 4.3;
3.8; s
s 8 _r 6% S- (3,5-J) initro-4-NiN ^T -dipropylssdnophenyl) -
-S-methyl-N-formylsulfoximine 133-135 Found for ^C 14 ^H 2O ^N 4 ^SO 6 45
45 , 2
• ⁶ ; η
; η 5.4
5.3 ; ν
; ν 15.1;
14.9 y S- (3-BroE-4-hydroxyphenyl) -S-methyl-N-tosyl-
sul-f oxirzin 178-180 Ber.
Found for ^C 14 ^H 14 ^NS 2 ° 4 ^Br ; 41
41 .6
J2 ; η
; η 3.5
3.5 ; ν
; ν 3.5%
3.4% S- (3,5-1) ibrcin ~ 4-hyd.roxyphenyl) -S-! Nethyl-N-
tosyl-sul-f cximin 190-191 Ber.
Found for C ₁₄ H ₁₃ NS ₂ O ₄ Br ₂ 34
34 ; η
; η 2.7
2.7 ; N
; ν 2.9%
2.8% S.
S. 12.9%
12j8% S- (4-Cf) lor-phen y J) -S-rae thy 1-N- (N * -methyl-
¹ csrbasioyl) sul -f .oiiiain 141-143 Ber.
Found for C ₉ H _n N ₂ SO ₂ :
4th 43
44 , 7
r ° ; η
; η 4.4 ; ν
; ν 11.3;
Ujl; : C '! S : C
: C : C
: C : C
: C C.
: C : C
: C . C.
C. C.
C. : C
": C C.
C.

cn 1

Continued TABLE I:

link Ports, too
F. ⁰ C ■ τ ABEL LE I analysis 25.6; H
26 ₇ O; H 2.2
V- 21 29 ( 371 ; s
; s 3 . P.
I. S- (3,5-pibromo- 4-hydroxyphenyl) -S-methyl-
suIt .oxinin : C
: C 28.0; H
27.6; H 3.0
2.9 ; ν
; ν 4.3
4j0 ; Br
; Br 48.6%
48 _? 9% S- (3-rom-4-hydroxyphenyl) -S-methyl-
sul-Γ oxininiunt sulfate Ber
Found . for C ₇ H ₇ NSO ₂ Br ₂ , = ^c
■: C 49.1; H
49.4; H 5.3
5.4 ; ν
; ν 4.7
4.2; ; s
, S. 16.0%
15.7% _ ^ S- (4-hydroxyphenyl) -S-ir.ethyl sulfoximin
O Ber.
Found for ^C 14 ^H 18 ^N 2 ^S 3 ° 6 ^Br ; : C
: C 40.8; H
41.7; H 5.6
5.9 ; ν
; ν 8.2
7.8 ; s
; s 18.7%
18.3% °° S- (4-i) iäthoxypfaosphinothioyloxyphenyl) -S-
methyl sulf oxicin Ber.
Found for C ₇ H ₉ NSO ₂ : C
: C 45.2; H
44.8; H 5.1
5.2 ; ν
; N 4.3,
4.9 , P
; ρ 9.6%
9.1%, _ _i S- (4-Diathoxyphosphinothioyloxyphenyl) -S-
CD methyl-N-tosylsulf .oximin Ber.
Found for' C _n H ₁₈ PNS ₂ O ₄ : C
: C 37.3; H
36.5; H 3.1
3> 1 ; ν
; ν 2.9
2.7 ; ρ
; P. 6.5% ^!
6.4% ^OT S- (4-ft ydroxy-3-j .od-phenyl) -S-methyl-N-
tosylsulf oximin Ber.
Found for ' ^C 18 ^H 24 ^PNS 3 ° 6 : C
: C 29.1; H
30.0; H 2.3 ; ν
; ν 3.1%
2 ^ 8% BATH 5 - (. 3,3-Dl ^ öd -4-hydroxyphenyl) -S-methyl-N-
tosylsulf oxindn Ber.
Found for C ₁₄ H ₁₄ NS ₂ O ₄ I. : C
: C 19.9; H
20.2; H W.
2.2 ; ν
; ν 2.4%
2.2% - ORiGIi S- (3,5-Dijod-4-hydroxyphenyl) -S-methyl-
. sul-f.oxiain. Ber.
Found for C ₁₄ H _n NS ₂ O ₄ I ₂ C.
C. 19.9; H
19.8; H 1.7
1.6 ; ν
; N 3.3%
2.8% S- (3,5-DiJ cd -4-hydroxyphenyl) -S-methyl-
sulτ oxicin (zwitterion) Ber.
Found for C ₇ H ₇ NSO ₂ I ₂ : C.
C. 47.1; H
46.5; H 5.0
4.8 ; ν
; ν 3.3%
2.9% S- (3,5-Dinitro-4-N; N ^t -dipropylaminophenyl) -S
methyl-N-phenylsulphonylsulphoximine Ber.
Found for C ₇ H ₇ NSO ₂ I ₂ : C.
C. 46.4; H
45.6; H 5.5
5.7 ; ν
; ν 13.27
13.03 ψ h-C2 _f 5-D: .r.icro-4-ethane oul { oxiaanophenyi) -
l IsWipropylamoaira ^ -toluOl-sulf "oiiat
-i ■ _> ■ 3 series.
Found for C ₁₉ H ₂₄ N ₄ S ₂ O ₇ : C.
C. ; ν
; ν 10.8
11.0 12j4%
12.3% 217-218 £> he.
Found for ^C 20 ^H 28 ^N 4 ^S 2 ° 8 y 223-225 205-207 oil 75-77 172-175 204-206 235-235
(Decomp.) 215-217
(Decomp.) 163-165 115-118

Example 10 Herbicidal effect

To test the herbicidal action, the inventive Compounds tested against a representative selection of the following plants: Maize, Zea mays (Mz); Oats, Avena sativa (0); Eaigras, Lolium perenne (RG); Pea, Bsum sativum (P); Flax, Linum usitatissium (L); Mustard, Sinapis alba (M); and sugar beet, Beta vulgaris (SB).

The tests were carried out in two groups as pre-emergence tests and post-emergence tests. The pre-emergence attempts consisted in spraying a liquid formulation of the compound on the floor in which the seeds of the plant species mentioned had been sown shortly before. The post-emergence attempts consisted of two Experimental groups, namely the impregnation of the soil and foliar spray experiments. When the soil was soaked, the soil in which seedlings of the plant species mentioned grew, soaked with a liquid formulation, the one according to the invention Compound included. In the foliar spray tests, seedlings of the plants were grown with such Sprayed formulation.

The soil used in the trials was steam sterilized modified John Innes Compost in which half of the peat had been loosely replaced with vermiculite.

The formulations used in the tests were prepared by the compounds with water and thinned ver solutions of the compounds in acetone containing 0.4 wt .-% were used of an alkylphenol-ethylene oxide condensate (Triton X 155). In the spray tests on the ground and on the leaves, the acetone solutions were

- 20 109853/1975

Chen volume of water was diluted and the formulations obtained were in two doses corresponding to 10 and 1 kg of active ingredient applied per hectare in a volume corresponding to 400 liters per hectare. In the soil impregnation tests, one volume of the acetone solution diluted to 155 volumes with water and the formulations obtained in a dosage corresponding to 10 kg of active ingredient applied per hectare in a volume corresponding to around 3,000 liters per hectare.

In the pre-emergence tests, the untreated was sown Soil and in the post-emergence tests untreated soil with plant seedlings tested as comparison tests.

The herbicidal effects of the compounds were checked visually 7 days after spraying the leaves and watering the soil and 11 days after spraying the soil and entered on a scale from 0 to 9. A rating of 0 shows no effect on the treated plants, a rating of 2 shows a reduction in the fresh weight of stems and leaves of the plants of about 25%, a rating of 5 shows a reduction of about 55 % and a rating of 9 a reduction of 95 %, and so on . at*

The test results are given in Table II below.

In the trials with certain compounds, oats were found replaced by rice oryza sativa (R) and ryegrass by barnyard millet Echinochloa crusgalli (BG). The results of this Experiments are given in Table III.

- 21 -

109853/1975

TABEL

II

-.S.

link H H ^X 3 ^X 4 ^R 2 ^R 3 Do-
sis
Kg / ha Nachlauflaüf '- (plants) Leaf spraying Pre-emergence H H H H ^C 6 ^H 5 H Soaking the soil Mz 0 RG P L M SB Floor spraying H H «2 H CH ₃ H ΊΟ j
1 , Mz 0 RG P L M SB 0 2 117 6 6
- 0 0 0 3 2 2 Mz 0 RG P L M SB H H ci H CH ₃ COCH 10 '
1 0 1 0 0 3 2 0 13 7 14 9 9
11 0 0 3 7 7 0 1 0 0 0 0 0
- 0 - - - - H H CH ₃ H CH ₃ H 10
1 0 2 5 0 0 3 4 0 2 117 6 3
- 0 0 0 11 0 0 0 10 0 4 0
- - 0 - - 0 - Cl H 2 H CH ₃ COCH ₃ 10
1 0 0 0 0 0 0 0 11 12 8 8 6
0 0 0 0 6 7 6 0 0 0 0 0 0 0 Cl H NO ₂ H CH ₃ H 10
1 0 0 0 0 0 0 0 0 6 4 18 9 7
- 0 0 0 5 6 0 0 0 0 0 0 0 0 I ^N0 2
ro H NO ₂ H CH ₃ COCH ₃ 10
1 0 0 2 0 0 1 0 3 6 6 8 9 9 9
1 .2 0 14 9 3 0 0 0 0 0 -1 0
- - - - - ο H Cl H CH ₃ H 10
1 0 0 0 0 0 0 0 13 12 7 9 4
0 0 0 0 2 7 2 0 0 0 0 0 0 O Cl H CH ₃ H 10
1 0 0 0 0 0 0 0 8 7 8 3 9 9 9
1110 8 8 2 0 0 0 0 0 0 0 10
1 6 0 3 0 0 0 0 0 1 14 4 8 6
- 0 0 0 0 2 0 6 0 7 0 3 7 1
0 - 0-00 0 0 1 0 0 10 0 0 1 0 0 0 0 0
- 0 - - - -

TABLE III

- Link H ^Χ 2 X ₃ ^Χ 4 ^R 2 ^R 3 do
sis
kg /
Ha Post-emergence (plants) Leaf spraying Run ahead. · · - H NO ₂ N (C ₃ H ₇ ) ₂ NO ₂ CH ₃ H 10
1 Soil watering Mz R BG P L M SB Floor spraying NO ₂ B. H H CH ₃ H 10
1 Mz R BG P L M SB 8 7 8 5 7 8 5
0 2 1 0 2 3 0 Mz R BG P L M SB B. B. SO ₂ H CH ₃ Cl 10
1 7 5 7 0 0 0 0
1 7 8 9 4 9 9 9
2 2 7 0 8 9 7 8 8 9 05 7 8
3 6 9-02 5 B. NO ₂ Cl H CH ₃ H 10
1 5 4 8 18 8 6 2 4 8 18 9 8
0 17 0 1 .8 1 8 9 9 16 8 6
0 7 10 0 1 2 H B. NO ₂ H CH ₃ CON (CH ₃ J ₂ 10
1 0 03 0 0 2 0 2 6 8 15 9 5
0 16 0 15 0 0 6 6 0 0 6 2
- 0 0 - - 0 0 B. B. Cl B. CH ₃ OCOC ₂ H ₅ 10
1 0 0 0 0 0 0 0 1 2 8 - 9 9 7
0 0 4 - 2 6 1 0 0 0 0 0 0.0 ¹ B B. NO ₂ B. CH ₃ CONHC ₂ H ₅ 10
1 0 0 5 - 0 0 0 0 3 6 2 6 5 4
- 0 0 0 0 11 0 0 3 2 6 4 2
- - 0 0 0 0 O 1 0 1 0 0 0 1 1 2 8 0 4 9 2
0 0 0 - 0 2 0 0 0 ^# 1 0 0 0 0
- - ο - - - ■ - 0 0 0 0 0 0 0 0 0 0 0 0 2 0
- - - _ _ 0 -

^X l ^X 2 Cont.: V H SU T 1 Mz Ju E. Ill BG P. L. M. SB Mz Leaf spraying BG P. L. M. SB 21 29678 Mz R. BG P. L. M. V H NO ₂ link NO ₂ CH ₃ Do-
sis
Kg / he .- ι 6th 0 1 6th 0 1
0 R. 6th
1 1
0 9
7th δ
6th 2
0 2
0 δ
0 9
0 0
Γ- 0 4th
0 ι H NO ₂ NO ₂ CH ₃ I Λ 7th 6th 0 0 0 0 6th
0 0 5
1 0 3
0 3
0 0 Yor casserole 7th
3 9
7th 9
9 0 0 CM ΐ-Ι * H NO ₂ NHC ₃ H ₇ NO ₂ CHn H 10
1 3 4th 0 0 0 0 1
0 4th
0 2
0 0 1
0 3
1 0 6th
0 9
2 9
2 0 0 3
0 SB H NO ₂ N (C ₃ H ₇ ) 2 NO, CH ₃ COCH ₃ 10 '
1 1 Nacnauflauf (plants) 2 0 0 0 0 0 3
0 1
0 0 0 0 0 2
0 δ
0 9
2 1
0 0 0 2
ρ σ
co H NO ₂ N (C ₃ H ₇ O ₂ NO ₂ CH- CONHCH ₃ 10
1 6th Soil watering 3 0 0 0 0 0 2
0 0 0 3
0 2
0 0 Floor spraying 1
0 δ
0 9
1 0
0 0
0 0
0 4th
1 00
cn
co -H NO ₂ N (C ₃ H ₇ ) 2 NO ₂ CH ₃ COCH ₂ Cl 10
1 6th R. 4th 0 0 0 0 2
0 1
0 2
0 0 0 0 0 2
0. CO CM 9
7th 0 0 1
0 7th
0! —Ι
OK H NO ₂ N (C ₃ H ₇ ) 2 NO ₂ CH ₃ COcyclo-
propy1 10
1 1 6th 3 0 1 8th 0 0 1
0 2
0 0 6th
1 7th
1 2
0 5
0 δ
0 9
0 0 0 2
0 \
7th
0 tr « H NO, N (C ₃ H ₇ ) ₂ NO ₂ CH ₃ COC ₂ H ₅ 10
1 6th 6th 6th 0 0 0 2 3
0 0 5
1 0 4th
0 4th
0 1
0 δ
δ 9
9 9
9 0 4th
1 5
1 5
1 H Br NHC ₃ H ₇ Br CH ₃ COCH ₃ 10
1 - 5 ■ - - - - - 0 4th
1 4th
0 0 7th
1 00 VO 9
9 4th
0 9
0 2
0 0 δ
2 6th
0 7th
1 H
I.
ru NO ₂ N (C ₃ H ₇ ) ₂ NO ₂
ToIu CH ₃
olsu COH / 10
1 - 4th ··· - - - - 4th
0 2
0 00 r-l I 1
0 7th
4th δ
0 1
0 U) OO δ
7th I OO VO 0 7th
0 3
0 4th
0 OH H 10
1 5 5
0 9
6th N (C ₃ H ₇ ) ₂
P- H
lfonat 10
1 5 7th
0 3 7th
0 5 - -

TABEL

NI

■ 3. '

link dose
Kg / ha Post-emergence (plants ) Blade tip Pre-emergence (seedl ^ 1
Ό ^R 3 10
1 Floor drainage Mz R BG P L M SB Floor spraying -CONH ^ \
CH ₃ 10
1
Mz R BG P L M SB 0 0 0 2 4 7 7
- - - 0 1.31 Mz R, BG P L M SB COOCH ₂ C ₆ H ₅ Ό 0 0 13 6 5 0 0 0 12 5 2
- - 0 0 0 0 0 17 0 19 4
0 0 - 0 1 0 0 0 0 111 0 0 17 10 11
- ■ 00 0-00

Be i s ρ i e 1 11 Insecticidal and acaricidal effects

The insecticidal action and the acaricidal action of the compounds according to the invention were tested as follows.

I. It was a solution of 1 wt .-% of the compound in Acetone prepared and taken up in a micrometer syringe. ' Adult female houseflies (Musca domestica) (two at a time) was anesthetized with carbon dioxide and a 1 yul drop was wiped off the lower abdomen. A total of 20 flies were treated. The treated flies were kept in glass jugs for 24 hours each contained some granular sugar as feed. The percentage of dead and dying flies was thereafter recorded.

II. In each case 0.1 ml of a 1% strength by weight solution of the test compound in acetone were placed in a beaker 100 ml of water mixed. Twenty mosquito larvae (Aedes aegypti) were found that were 5 to 6 days old (4th molt) placed in the glass and kept the beakers for 24 hours.

The percentage of dead and dying larvae was then given.

III. The compounds were prepared as solutions or suspensions in water containing 20% by weight of acetone and 0.05% by weight of Triton X set as a wetting agent. The solution contained 0.7% by weight of the test compound. There were plants of beets and of thick beans, each cut to a leaf, sprayed on the underside of the sheet with the formulations in each case.! The spraying was carried out with a spray machine carried out, which delivered 1.14 l / ha, with the plants were guided under the spray jet on a conveyor belt.

~ 26 -

109853 / 197S

Ten diamond moth larvae (Plutella maculipennis) (4th moult) or ten adults became eight days old 1 to 2 week old mustard beetles (Phaedon cochleariae) on the sprayed leaf of each beet plant and ten sucking (6 days old) sweet pea mites (Megoura viciae) placed on the sprayed leaf of each bean plant. the Plants were enclosed in the glass cylinder, which was closed on an oath with muslin. The mortality was counted after 24 hours.

IV. In tests against greenhouse spider mites (Tetranychus urticae), leaf disks were made from plants from French Beans cut out and sprayed according to III. One hour after spraying, the disks with ten adult ones Mites occupied. Mortality was counted 24 hours after occupation.

V «In experiments with larvae of the great cabbage white butterfly (Pieris brassicae) leaf disks from cabbage leaves were sprayed in the manner described under III. There were ten 8 to 10 day old caterpillars (3rd molt) are placed on the discs between Petri dishes. The mortality was counted 24 hours after occupation.

The results of these tests are given in Table V below, with A complete destruction and B partial destruction and 0 means no killing of the test insects.

10985 3/197 5

TABEL Y.

Connection M.domestica A.aeRypti P.chochlearia P.maculipennis P.brassicae M.viciae T.urtdcae

S.S-tetramethylene- (IT'tll

(y A C C C-CB

carbamoyl) sulfoximine ■. .

S, S-tetramethylene

Έ- (benzyloxycarbonyl) -

sulfoxime AB ^- CC - CA

S- (3,5-dibromo-4-hydroxy-

O ₀ phenyl) -S-methyl-IT-

( Xitosylsulf oximin CCC; .C - AC

"^ S- (3,5-dibromo-4-hydroxy-. W

- "phenyl) -S-methyl-

«° sulfoximine C C C C - A. C '

^m S- (4-diethoxyphosphinothioyl oxyphenyl) -S-methylsulfoximine AA ABA AA

S- (4-diethoxyphosphino-

thioyloxyphenyl) -S-methyl-

N-1 ο sylsulf oximin C C A A AAA

S, S-Diphenyl sulf oximine C C. C C - B A

:, Fsj—

NJ) CO

I CD

Claims (1)

PATENT CLAIMS 1) Herbicides and pesticidal agents from a carrier or a surfactant or both a carrier such as a surfactant and an active ingredient, characterized by a content of a sulfoximine derivative the general formula: V (D % 2 ° in Η ,, an optionally substituted aryl group, R ₂ is an alkyl or aryl group, or R ^ and R _p together represent a polymethylene group, and R, a hydrogen or halogen atom or a nitro or acyl group, _or a salt of these compounds as an active ingredient . 2) Means according to claim 1, characterized by a content of a sulfoximine derivative of the formula I, in which R ^ is a phenyl group, optionally by one or more halogen atoms, one or more nitro groups. Or a hydroxy, alkyl, alkylamino, dialkylamino -, or Dialkylphosphorothionatgruppe is substituted, R _{2 is} an alkyl group with 1 to 6 carbon atoms or a phenyl group or R ^ and R ₂ together a polymethylene group with up to 5 carbon atoms and R, a hydrogen or chlorine atom, a nitro group, an optionally chlorinated alkanoyl group with Λ to 6 carbon atoms, a cycloalkylcarbonyl group with up to 6 carbon atoms, an aroyl group, an N-substituted or N, N-di- - 29 109 8.5 3/197 5 substituted carbamoyl group, an alkoxycarbonyl group, an aralkoxycarbonyl group, an (alkylthio) carbonyl group or an alkyl, aryl or alkarylsulfonyl group, or a sulfate or alkaryl sulfonate of these compounds, as an active ingredient. 3) means according to claim 2, characterized by a content of a sulfoximine derivative of the formula I, in the R ^ a phenyl group, optionally by a or more chlorine, bromine or iodine atoms, one or more nitro groups or a hydroxy, methyl, propylamino, Dipropylamino or diethylphosphorothxonate group is substituted, Ro is a methyl or phenyl group or R ^ and Ro together is a tetramethylene group and R ^ is a hydrogen or Chlorine atom or a nitro, formyl, acetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, propionyl, Dichloropropionyl, butyryl, isobutyryl, cyclopropylcarbonyl, Benzoyl, methylcarbamoyl, ethylcarbamoyl, phenylcarbamoyl, chlorophenylcarbamoyl, dichlorophenylcarbamoyl, Tolylcarbamoyl, dimethylcarbamoyl, ethoxycarbonyl, Benzyloxycarbonyl-, (ethylthio) carbonyl-, methylsulfonyl-, Denotes phenylsulfonyl or tosyl group, or a Sulfate or toluenesulfonate of such a compound as an active ingredient. 4) Agent according to claim 3, characterized by a content of a sulfoximine derivative of the formula I, in the R ^, a phenyl group, optionally through substituted one or more chlorine atoms or one or more nitro groups or a methyl or dipropylamino group is, Rp is a methyl or phenyl group and R ^ is a hydrogen or chlorine atom or a nitro, Acetyl, methylcarbamoyl, ethylcarbamoyl, phenylcarbamoyl, Chlorophenylcarbamoyl, dichlorophenylcarbamoyl, dimethylcarbamoyl, Ethoxycarbonyl or (ethylthio) carbonyl group means as an active ingredient. - 30 - 10985 3/197 5 5) Agent according to claim 1, characterized by a content of S- (3,5-dinitro-4-N ', N'-dipropylaminophenyl) -S-methylsulfoximine as an active ingredient. 6) means according to claim 1 to 5 »marked through a formulation form as powder, dust preparation, Granulate, solution, emulsifiable concentrate, emulsion, concentrated suspension or aerosol. SuIf oximine compounds of the formula I in which K, -, E ₂ and L have the meaning given in claim 1, or their salts, with the proviso that when R 1, R ₂ each represent a phenyl group or together represent a tetramethylene group or R ^ is a phenyl group substituted in the 4-position by a chlorine atom, a nitro group or a methyl group and R _{2 is} a methyl group, R, is not a hydrogen atom. 8) SuIfoximinverbindungen according to claim 7 »in the formula IR ^, a phenyl group which is optionally substituted by one or more halogen atoms, one or more nitro groups or a hydroxy, alkyl, alkylamino, dialkylaminο or dialkylphosphorothxonate group, R _{2 is} an alkyl group with 1 to 6 carbon atoms or a phenyl group or R ,, and R ₂ together a polymethylene group with up to 5 carbon atoms and R, a hydrogen or chlorine atom, a nitro group, an optionally chlorinated alkanoyl group with 1 to 6 carbon atoms, a cycloaxkylcarbonyl group with up to 6 carbon atoms, an aroyl group, an N-substituted or N, N-disubstituted carbamoyl group, an alkoxycarbonyl group, an aralkoxycarbonyl group, an (alkylthio) carbonyl group or an alkyl, aryl or alkarylsulfonyl group, or a sulfate or alkarylsulfonate of these Link. - 31 - 1098-53 / 197 5 9) sulfoximine compounds according to claim 8, characterized _} that in formula IE ^. a phenyl group which is optionally substituted by one or more chlorine, bromine or iodine atoms, one or more nitro groups or a hydroxy, methyl, propylamino, dipropylamino or diethyl phosphorothionate group, E ~ a methyl or phenyl group or E, and Ep together a tetramethylene group and B, a hydrogen or chlorine atom or a nitro, formyl, acetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, propionyl, dichloropropionyl, butyryl, isobutyryl, cyclopropylcarbonyl, benzoyl, Methcarbamoyl, ethylcarbamoyl, phenylcarbamoyl, chlorophenylcarbamoyl, dichlorophenylcarbamoyl, tolylcarbamoyl, dimethylcarbamoyl, ethoxycarbonyl, benzyloxycarbonyl, (ethylthio) carbonyl, methylsulfonyl, or a tosulfonyl group, or one of these compounds, or a tosulfonyl group, or a tosulfonyl group, or a methylsulfonyl or a tosulfonyl group, or tolosulfonyl or a tosulfonyl group, or one of these compounds. 10) sulfoximine compounds according to claim 9 »characterized in that in formula IE _x . a phenyl group which is optionally substituted by one or more chlorine atoms or one or more nitro groups or a methyl or dipropylamino group, E ^ a methyl or phenyl group and E, a hydrogen or chlorine atom or a nitro, acetyl, methylcarbamoyl, ethylcarbamoyl , Phenylcarbamoyl, chlorophenylcarbamoyl, dichlorophenylcarbamoyl, dimethylcarbamoyl, ethoxycarbonyl or (ethylthio) carbonyl group. , 11) S- (3,5-Dinitro-4-N ', N'-dipropylaminophenyl) -S-methylsulfoximine. 12) Process for the preparation of sulfoximine compounds according to claim 7, wherein 'in formula IB _{5 represents} a hydrogen atom, characterized in that one - 32 - 10 9 & 5 3/1975 - 32 a sulfoxide of the formula: "SO. (II) reacted with hydrazoic acid. 13) Method according to claim 12, characterized in that one is the hydrazoic acid generated in situ under the action of an acid on an alkali metal azide. 14) Method according to claim 1'3, characterized in that the acid and sulfuric acid used as alkali metal azide sodium azide. 15) Process according to claim 12 to 14, characterized in that the reaction is carried out in
an organic solvent. 16) The method according to claim 15, characterized in that g e k e η η, that chloroform is used as the solvent. 1.7) 'process for the preparation of sulfoximine compounds according to claim 7, wherein in formula IE ^ an acyl group
represents, characterized in that the corresponding compound in which E is a hydrogen atom is reacted with an acyl halide. 18) Method according to claim 17, characterized in that the acyl halide is an acyl - 33 109853/1975 Chloride used. 19) Process according to claim 17 "to 18, characterized in that the reaction is carried out in the presence an acceptor for hydrogen halide. 20) Method according to claim 19, characterized in that one is used as an acceptor for hydrogen halide a tertiary amine is used. 21) Process according to claim 20, characterized in that the tertiary amine is triethylamine or pyridine is used. 22) Process according to Claim 17 to 21, characterized in that the reaction is uaß in an organic solvent. 23) Method according to claim 22, characterized in that the solvent used is ether. 24) Process for the preparation of sulfoximine compounds according to claim 7 * wherein in formula I R, a halogen atom means, characterized in that the corresponding compound in which R is a hydrogen atom is reacted with a halogenating agent. 25) Process according to claim 24, characterized in that one is used as the halogenating agent the elemental halogen or an alkali metal hypohalite is used. 26) Process for the preparation of sulfoximine compounds according to - 34 ■ 109853/1975 J claim 7 wherein in formula IR, a nitro group, characterized in that _t the corresponding compound in which E ^ is a hydrogen atom, is nitrated with a mixture of nitric acid and sulfuric acid. 109853/1975