DE1670275C - Salts of benzo 2,1,3 thiadia zinon (4) 2 2 dioxyden and growth regulating agents containing them with simultaneous herbicidal action - Google Patents

Description

CH ₃ j

IO

15th

in which R _{1 is} a lower alkyl radical, R _{2 is} a / I-Halogenäthylrest and X is a methyl or an amino group.

2. Growth regulating agent with herbicidal action, consisting of a compound according to Claim 1 and customary diluents and / or carriers.

3. Use of a connection according to claim J as a growth-regulating agent with a herbicidal effect.

3 ° It is known that 2-chloroethyl-trimethylammo-

nium chloride (CCC) inhibits the growth in length of summer and winter wheat with simultaneous thickening of the stalk and thus an increase in stability the faucet works. However, 2-chloroethyl-trimelhylammonium chloride does not cause weeds and there is a danger that these will overgrow the wheat. For efficient wheat cultivation Simultaneous use of CCC and herbicides is therefore essential. Mixtures of 2-chloroethyltrimethylammonium chloride with herbicides, however, can only be produced immediately before application and cannot be stored (J. Stryckers and M. Van Himme, Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent, 31 [1966], No. 3, pp. 1132 and 1154), a separate one Spreading, however, is technically uneconomical.

It has now been found that salts of benzo-2, l, 3-thiadiazinon- (4) -2,2-dioxides the general formula

55

60

in which R _{1 is} a lower alkyl radical, R _{2 is} a / i-haloethyl radical and X is a methyl or an amino group, in wheat and barley the length growth such as 2-chloroethyltrimethylammonium chloride and at the same time a good herbicidal effect against dicotyledonous weeds, especially against chamomile, to have.

CH ₃ ; l R ₂ -NX I. O
Il
/ C _x CH ₃ NR ₁ I. SO, \ / ^N N ^/ Θ

The active ingredients according to the invention are new. For example, they can be easily prepared by reacting the sodium salts of the corresponding benzo - 2,1,3 - thiadiazinon - (4) - 22 - dioxides with 2 - chloroethyl - trimethylammonium chloride or N - 2 - chloroethyl - N, N - dimethyl - hydrazonine chloride produce. Since all compounds according to the invention can be prepared by appropriate processes, the preparation of the

2 - chloroethyl - trimethylammonium salt of 3 - n-propyl - benzo - 2,1,3 - thiadiazinon - (4) - 2,2 - dioxides described in more detail below.

26 parts by weight of 3 - η - propyl - benzo - 2,1,3 - thiadiazinon - (4) - XL - dioxide sodium salt are dissolved in 200 parts of methanol. A solution of 13.5 parts of 2-chloroethyl-trimethylanmionium chloride in 100 parts of methanol is allowed to flow into this solution at room temperature. This mixture is stirred at 60 ° C. for a further 3 hours to complete the reaction. After cooling, the separated sodium chloride is filtered off with suction and the filtrate is evaporated to dryness in the vacuum of a water jet pump. 36.2 parts of white crystalline salt remain, which dissolves in clear water without hydrolysis.
Analysis: C ₁₅ H ₂₄ ClN ₃ O ₃ S (361.9).

Calculated ... Cl 9.80, N 11.61, S 8.86;

found .... Cl 9.7, N 11.5, S 8.8.

The compounds according to the invention are colorless crystalline salts which are soluble in water without decomposition are.

The thiadiazinone compounds required as starting materials for the preparation of the compounds according to the invention can be easily known per se by cyclizing N-alkyl-N'-ocarboxyphenylsulfamides or N - alkyl-N'-o-carboalkoxyphenyl sulfamides using condensation agents. As a condensing agent, for example, phosphorus oxychloride, thionyl chloride or aqueous or alcoholic Use alkaline solutions.

By reacting the compounds thus obtained with sodium methylate in methanolic solution and subsequent evaporation of the methanol in vacuo gives the corresponding sodium salt. For example, in this way one obtains from the

3 - η - propyl - benzo - 2,1,3 - thiadiazinon - (4) - 2 ^ - dioxide uas 3-η-propyl-benzo-2,1,3-thiadiazinon- (4) -2,2-dioxide-sodium salt.

The substances according to the invention can be in the form of their aqueous solutions, as emulsions, Suspensions or dusts are applied. They can also be incorporated into fertilizers. In any case, a fine distribution of the active substance should be guaranteed.

The following examples demonstrate the better effect of the active ingredients according to the invention the individual components or their simple (physical) mixtures.

example 1

In the greenhouse the plants were wheat (variety Opal and variety Koga II) (Triticum vulgare), chamomile (Matricaria chamomilla), glutinous herb (Galium aparinc), white goose foot (Chenopodium album), flea knotweed (Polygonum persicaria), small stinging nettle (Urtica urens) at a height of 2 to 10 cm (wheat

1st to 2nd sheet, 10 cm high) with 2 kg / ha of 2-chloroethyltrimethylanmiomunisalt of 3 - ethyl - benzo-2,1,3 - thiadiazmon - (4) - XL - dioxide (I), mixture of 1,23 kg / ha 3 - ethyl - benzo - 2,1,3 - thiadiazinon - (4) - XL - dioxide + 0.93 kg / ha 2 - chloroethyl - trimethylammonium chloride (II), 1.23 and 2 kg / ha 3 - Ethyl - benzo - 2 - thia - 1,3 - diazinon- (4) -2> dioxide (III), 0.93 and 2 kg / ha of 2-chloroethyltrimethylammonium chloride (TV), each dissolved in 6001 water per hectare, treated.

After 4 weeks, the herbicidal effect was tested and the height of the wheat was measured in centimeters. It was found that the 2-chloro

IO ethyl - methylammonium salt of 3 - ethyl - benzo - 2,1,3 - thiadiazinon - (4) - XL - dioxide (J) showed a growth inhibition on wheat with a good herbicidal effect at the same time. The mixture Π, consisting of 3 - ethyl - benzo - 2,1,3 - thiadiazinon - (4) -XL- dioxide and 2-chloroethyI-trimethyIammoniumchloride, showed a worse effect than the active substance L

3 - ethyl - benzo - 2,1,3 - thiadiazinon - '4) - 2,2 - dioxide (III) showed no growth inhibition in wheat, while the compound 2-chloroethyl-trimethylammonium chloride (FV) showed no herbicidal effect. The test result is from the following Table to see:

Application rate

control

(U.N-

treated) 0

II 1.23 III

+ 0.93 IV Active ingredient III

1.23 j 2

kg / ha

0.93

IV

kg / ha

Useful plants:

wheat

(Variety opal)

wheat

(Variety Koga II)
Weed plants:

chamomile

Sticky herb

White goosefoot

Flea Knotweed ...

Small stinging nettle

0
0
0
0

16

16 to 17

100

70 to 80 90 to 100 70 to 80

100

18th

19th

80 60 to

80

60 80 to 21

21

70 to 80
60 to 70
70 to 80

60
80 to 90

20 to 21

20 to 21

100

70 to 80
90 to 100
70 to 80
90 to 100

17 to 18

10 to 20

16 to 17 cm

16 to 17 cm

20th

10 10 to 20

20 20 to 30

100 = total destruction of weeds. 0 = no weeds are killed.

In the case of wheat, the height of the plants was measured in centimeters. The herbicidal damage to the wheat was 0 in all cases. Example 2

Result of the length measurement

40

Wheat plants of the "Heines Koga" variety and barley plants of the "Breuns Wisa" variety were in New building shells in a sandy loam soil with appropriate nutrient supply and with supply attracted by 3 and 12 mg each of the new active ingredients. The active ingredients 2-chloroethyl trimethylammonium salt of 3-methyl-benzo-2, l, 3-thiadiazinon- (4) - 2,2 - dioxide (I), 2 - chloroethyl - trimethylammonium salt of 3 - ethyl - benzo - 2,1,3 - thiadiazinon - (4) - 2,2 - dioxide (II), 2 - chloroethyl - trimethylammonium salt des 3-propyl-benzo-2,1,3-thiadiazinon- (4) -2,2-dioxide (III) were immediately after the Seed in an aqueous solution is sprayed onto the surface of the soil. In addition to untreated control batches, 2-chloroethyl-trimethylammonium chloride = CCC was used as Reference substance included in the tests.

Just a few days after emergence, the treated plants showed a comparison with the control reduced growth in length and a noticeably darker blue color (increased chlorophyll content). While the effect of the compounds according to the invention on wheat largely corresponded to that of CCC, there was more shortening in length growth in barley than through treatment with CCC. These observations were supported by those made after an 18 day growth period Length measurements are confirmed. 100 plants were measured from each series of treatments.

Active ingredient

control
(untreated)

CCC

CCC

I.

I.

II

II

III

III

Application rate

mg of active ingredient per bowl

3
12th

3
12th

3
12th

3
12th

21.9

17.5
15.4
17.2
15.5
17.2
15.9
17.8
16.4

100

80 70 79 71 79 73 81 75

Barley plant height

16.5

16

15.5

15.5

15.0

15.5

14.5

16

13.5

97 94 94 91 94 88 97 82

Example 3

The plants wheat (variety »Opal«) (Triticum vulgare), chamomile (Matricaria chamonilla), Glutinous herb (Galium aparine), mustard (Sinapis arvensis) and pointed burdock (Xanthium spp.) at a height of 3 to 12 cm (wheat 1st to 2nd leaf, 11 cm height) with 3 kg / ha of the active ingredients each

I 2 - chloroethyl - trimethylammonium salt of 3 - methyl - benzo - 2,1,3 - thiadiazinon - (4) - 2,2-dioxide,

II 2 - chloroethyl - trimethylammonium salt of 3-ethyl-benzo-2, l, 3-thiadiazinon- (4) -2 ^ -dioxids

(M.p. 96-97 ° C),
LtI 2 - chloroethyl - trimethylammonium salt of 3-propyl-benzo-2,13-thiadiazinon- (4) -2,2-di-

oxides,
FV 2 - chloroethyl - trimethylammonium salt of 3 - isopropyl - benzo - 2,1,3 - thiadiazinon-

(4) -2 2-dioxide. n £ = 1.5410, V 2 - chloroethyl - trimethylammonium salt of 3 - butyl - benzo - 2,1,3 - thiadiazinon - (4) - Xl - di-

oxides,
VI N, N - dimethyl - N - β - chloroethyl - hydrazonium salt of 3 - methyl - benzo - 2,1,3 - thiadiazinon- {4) -2 ^ -dioxids,

VII Ν, Ν - dimethyl - N - β - chloroethyl - hydrazonium salt of 3 - ethyl - benzo - 2,1,3 - thiadiazinon- (4) -2 £ -dioxide,

VIII Ν, Ν - dimethyl - N - β - chlorathyl - hydrazonium salt of 3 - propyl - benzo - 2,1,3 -thiadiazinon- {4) -2 ^ -dioxids, /

IX Ν, Ν - dimethyl - N - β - chloroethyl / hydrazonium salt of 3 - isopropyl - benzo - £ 1,3 - thiadiazinon - (4) - XZ - dioxide. Mp. 116ybis 120 ⁰ C, X Ν, Ν - dimethyl - N - β - chloroethyl - hydrazonium salt of 3 - butyl - benzo - 2,1,3 - thiadipzinon- (4) -2 ^ -dioxids,
XI 2-chloroethyl trimethylammonium chloride,

each dissolved in 6001 water per hectare, treated. After 4 weeks, the herbicidal action against weeds was tested and the height of the wheat was measured. The test result can be seen from the following table. In the case of wheat, the height of the Plants measured in centimeters. The herbicidal damage to the wheat was 0 in all cases.

control
(untreated U) I. II Really
III material
IV V VI Wheat (variety opal)
chamomile 24
0 22nd
85 19th
100 20th
90 19 '
100 21
80 21
85 Sticky herb 0 80 90 85 100 80 SO Mustard 0 85 100 90 100 80 85 Pointed burdock type 0 80 100 90 100 80 80

Wheat (variety Opal) 24

Chamomile 0

Lapwort 0

Field mustard 0

Pointed chain type 0

= total destruction of weeds. = no weeds are killed.

Control (untreated)

VII

21 95 85 90 95

Active ingredient

VIII DC X Xl 22nd 20th 21 19th 85 95 80 25th 80 90 75 15th 85 95 8G 10 85 95 85 0

Claims (1)

Patent claims: 1. Salts of benzo-2, l, 3-thiadiazinou- (4) -2,2-dioxides the general formula CH ₃ " si
R ₂ -NX