DK143583B - PROCEDURE FOR COMBATING WEEDS AND MEANS FOR IMPLEMENTING THE PROCEDURE - Google Patents

Description

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| p (12) PUBLICATION <n) 11 + 3583 B

DIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM

(21) Application No. 1772/72 (51) IntCI.3 A 01 N 25/32 (22) Filing date 12 Apr. 1972 (24) Race day 12 Apr 1972 (41) Aim. available Oct. 17 1972 (44) Submitted Sep 14 1981 (86) International application no. - (86) International filing day - (85) Continuation day - (62) Master application no. -

(30) Priority 1 Apr 6 1971, 124868, US Dec 9 1971, 208041, US

(71) Applicant STAUFFER CHEMICAL COMPANY, New York, US.

(72) Inventor Ferenc Marcus Fallos, US: Mervin Edward Brokke, US:

Duane Randall Arneklev, US.

(74) Associate Company Chas. Hude.

(54) Weed control method and means for carrying out the process.

The present invention relates to a method and means for controlling weeds.

Among the many herbicides commercially available, thiol carbamates alone or mixed with other herbicides such as triazines have achieved a relatively high success. These herbicides ω are immediately toxic to a wide variety of weed species at different concentrations, which vary with the resistance of

Lf) the weed species. Some examples of these compounds are described in U.S.A. U.S. Patent Nos. 2,913,327, No. 3,037,853, No.

T-3,175,897, No. 3,185,720, No. 3,198,786, and No. 3-582,314. In practice, it has been found that the use of these thiol carbamates

ISLAND

143583 2 as herbicides on crops sometimes cause serious damage to the crop plant. By using the recommended amounts in the soil to control many broadleaf weeds and grasses, serious malformations and crippling occur on the crop plants. This abnormal growth of the crop plants results in loss of crop yield. Previous attempts to overcome this problem involve treating the crop seeds with certain antagonistic agents prior to planting, see U.S.A. U.S. Patent No. 3,311,509. The use of these antagonistic agents has not proved very successful.

It has now been found that plants can be protected from damage caused by thiol carbamates alone or in admixture with the above-mentioned compounds, and / or that the tolerance of the plants can be substantially increased to the active thiol carbamates by the method of the present invention which is peculiar by the characterizing part of claim 1.

The agent for use in the method according to the invention is peculiar to the characterizing part of claim 2.

The antidote compounds can be synthesized by mixing an appropriate acid chloride and an appropriate amine. If desired, a solvent such as benzene may be used. The reaction is preferably carried out at reduced temperature. After the reaction is complete, the final product is brought to room temperature and can be easily separated.

Example 1.

O CH9-CH = CH, CHCl0-C-iT 2 \ CH2-CH = CH2

A solution was prepared by dissolving 3.7 g (0.025 mol) of dichloroacetyl chloride in 100 ml of methylene dichloride, which was then cooled to ca. 5 ° C in an ice bath. Then 4.9 g (0.05 mol) of diallylamine was added dropwise while maintaining the temperature below ca. 10 ° C. The mixture was then stirred at room temperature for approx. 4 hours, washed twice with water, dried over magnesium sulfate, filtered and stripped. The yield was 4.0 g, n + = 1.4990.

Example 2.

O C-H-j-n n / 3 7 CHCl, -C-rN ^ i C3H7 ~ n

A solution was prepared by dissolving 3.7 g (0.025 mol) of dichloroacetyl chloride in 100 ml of methylene dichloride, which was then cooled to ca. 10 ° C in an ice bath. Then, 5.1 g (0.05 mole) of di-n-propylamine was added dropwise while maintaining the temperature below ca. 10 ° C. The mixture was then stirred at room temperature overnight, washed twice with water, dried over magnesium sulfate, filtered and stripped. The yield was 3.6 g, 30 n 2 = 1.4778.

Example 3

U y / CH3 ciici2-c-n ^ ch (ch3) -c £ ch

A solution was prepared by dissolving 3.7 g (0.025 mol) of dichloroacetyl chloride in 80 ml of methylene dichloride, which was then cooled to ca. 10 ° C in an ice bath. Then, 4.2 g (0.05 mole) of N-methyl-N-1-methyl-3-propynylamine in 20 ml of methylene dichloride was added dropwise while maintaining the temperature at about 10 ° C. The mixture was then stirred at room temperature for approx. 4 hours, washed twice with water, dried over magnesium sulfate, filtered and stripped. The yield was 2.9 g, n 2 = 1.4980.

Example 4

? J 1

Cn2Cl-C-NH-CN 2-jsv

A solution was prepared containing 100 ml of acetone and 5.05 g of furfurylamine (0.1 mole), then the solution was stirred with the addition of 7 ml of triethylamine at 15 ° C. Then 5.7 g of monochloroacetyl chloride was added and stirring was continued for an additional 15 minutes under which 500 ml of water was added. The reaction mass was filtered, washed with dilute hydrochloric acid and additional water and then dried to constant weight.

Example 5

U.S-

CHCl 2-c-NHY

n_Lch3

A solution of 5.7 g (0.05 mole) of aminomethylthlazole in 100 ml of benzene and 7 ml of triethylamine was formed. The solution was stirred at 10 ° C and then 5.2 ml (0.05 mol) of dichloroacetyl chloride was added dropwise. The mixture was stirred at room temperature for 10 minutes. Then 100 ml of water was added and the solution was washed with benzene solution, dried over magnesium sulfate and then evaporated to remove the solvent.

Example 6

O tr y.

·· / „_ CHC1 -ON '/ S Y i

X

'N-

A solution containing 200 ml of acetone and 17.5 g (0.05 mole) of 2-amino-6-bromobenzothiazole and 7 ml of triethylamine was formed. The solution was stirred at 15 ° C with cooling. Then, 5.2 ml (0.05 mole) of dichloroacetyl chloride was added slowly. This solution was stirred at room temperature for 10 minutes. The solid formed was filtered off, washed with ether, then with cold water and again filtered and dried at 40-50 ° C.

Example 7

O .11 "s n-C9H19" C "N'V

XCO ^^ - OCH

3.4 g of 3-methyl-3-butynylamine was dissolved in 50 ml of methylene chloride, 4.5 g of triethylamine was added and 7.6 g of decanoyl chloride was added dropwise with stirring and cooling in a water bath. After the reaction was complete, the mixture was washed with water and dried and the solvent removed by stripping to obtain 7.1 g of product.

Example 8.

CH <\? vCH2-CO-CH2 ^ CH-C-nC

CH 2 CH 2 -CH 3

A solution containing 5.9 g of diallylamine dissolved in 15 ml of methylene chloride and 6.5 g of triethylamine was formed. Then 6.3 g of cyclopropanecarbonyl chloride was added dropwise with stirring and cooling in a water bath. After the reaction was complete, the mixture was washed with water and dried and the solvent removed by stripping to obtain 8.2 g of product.

Example 9

.__ 0 CH0-CH = CH0

Q-K

- \ F ch2-ch <= ch2

A solution containing 4.5 g of diallylamine dissolved in 15 ml of methylene chloride and 5.0 g of triethylamine was formed. Then, 7.1 g of orthofluorobenzoyl chloride was added dropwise with stirring and cooling in an ice bath. After the reaction was complete, the mixture was washed with water and dried and the solvent removed by stripping to give 8.5 g of product.

Example 10. O

o CH2-CH2-OC-NH-CH3 Ciici2-Cn ^ X CH - - CEL - O- C-NH- CH - £ * L f of 26.3 g of diethanolamine with 37 g of diohloroacetyl chloride in the presence of 25.5 g of triethylamine in 100 ml of acetone. 6.5 g of N, N-bis (2-hydroxyethyl) dichloroacetamide, dissolved in 50 ml of acetone, were then reacted with 4 g of methyl isocyanate in the presence of dibutyltin = dilaurate and triethylamine catalysts. The reaction product was stripped under vacuum to give 8.4 g of product.

Example 11.

CH_ = CH-CII0 0 0 CH ~ -CH = CH ~ ά Δ> s tr ii Δ Δ J> NC-CH2-CN ^ CH2 = CII-CH2 ^ CH2-CH = CH2 7.8 g of diallylamine was dissolved in 50 ml of methylene chloride and dropwise added 8.5 g of triethylamine. Then 5.6 g of malonyl chloride was added dropwise with cooling and stirring. When the reaction was complete, the mixture was washed with water, dried over magnesium sulfate and stripped under vacuum to give 7.0 g of product.

Example 12.

CH0 = CH-CEL · 0 0 CH0 — CH = CH0 Δ Δ Ns. il ii Δ Δ

> N-C-CH2-CH2-C-N

CH2 = CH-CH2 ^^ 2-01 = ^ 2 7.9 g of diallylamine was dissolved in 50 ml of methylene chloride and 8.5 g of triethylamine was added dropwise. Then, 6.2 g of succinyl chloride was added dropwise with cooling and stirring. When the reaction was complete, the mixture was washed with water, dried over. magnesium sulfate and stripped in vacuo to give 9.7 g of product.

Example 13

CII3 0 / ch3 ch = c-ch-n-c-ch0-ch9-c-n * I! "" \

CH-O CH-C = CH

3 in CH 3 6.7 g of N 1 methyl-1-methyl-3-propynylamine was dissolved in 50 ml of methylene chloride and 8.5 g of triethylamine was added dropwise. Then, 6.2 g of succinyl chloride was added dropwise with cooling and stirring. When the reaction was complete, the mixture was washed with water, dried over magnesium sulfate and stripped under vacuum and 7.0 g of product was obtained.

Example 14.

/ —V o CH - CHNCH,

OK

vch2-ch * ch2 O = C-N (CH2-CH2 CH2) 2 7.9 g of diallylamine was dissolved in 50 ml of methylene chloride and 8.5 g of triethylamine was added dropwise. Then 8.1 g of o-phthalo = yl chloride was added dropwise with cooling and stirring. When the reaction was complete, the mixture was washed with water, dried over magnesium sulfate and stripped in vacuo to give 10.9 g of product.

Example 15

f \ W / \ °

CH-C-N-CH-CeCH

Qf -3 3.3 g of N-methyl-1-methyl-3-propynylamine was dissolved in 50 ml of methylene chloride and 4.5 g of triethylamine was added dropwise. Then, 9.2 g of diphenylacetyl chloride was added dropwise with cooling and stirring. When the reaction was complete, the mixture was washed with water, dried over magnesium sulfate and stripped under vacuum to yield 9.9 g of product.

Example 16.

2 2 \ = / ^ CH2> -CH = CH2

O = C-OH

4.9 g of diallylamine was dissolved in 50 ml of acetone and 7.4 g of phthalic acid = δ 143583 anhydride was added portionwise with stirring. The solvent was removed by stripping under vacuum and 13.0 g of product was obtained.

Example 17

/ v O CH «

{/ S-C-NH-C-C = CH

9.2 g of N (1,1-dimethyl-3-propynyl) 0-phthalamic acid was dissolved in 50 ml of methanol and 9.6 g of sodium methoxide. 25% aliquots of methanol were added with stirring and cooling. The solvent was removed by stripping or removed under vacuum resulting in 9.0 g of product. The intermediate N (1,1-dimethyl-3-propynyl) - O-phthalamate was prepared from 29.6 g of phthalic anhydride and 16.6 g of 3-amino-3-methylbutyn in 150 ml of acetone. The intermediate was precipitated with petroleum ether as a white solid and used without further purification.

Example 18.

° C2S5 CHCl2-C-N2

Xc2H5 3

A 500 cm 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then 7.7 g of diethylamine (0.105 mole), 4.0 g of sodium hydroxide solution and 100 ml of methylene chloride were charged to the flask and the mixture was cooled in a dry ice-acetone bath. Then, 14.7 g (0.10 mol) of dichloroacetyl chloride was added portionwise. The mixture was stirred for an additional 1 hour and immersed in an ice bath. It was then phase separated and the lower organic phase washed with two portions of 100 ml of dilute hydrochloric acid, twice 100 ml of sodium carbonate solutions, dried over magnesium sulfate and evaporated in vacuo to give 16.8 g of product.

Example 19.

CH2-CH = CH2 CH3-C3C-CH2-O-C-N4 CH2-CH * CH2 4.0 g (0.025 mol) of Ν, Ν-diallyl carbamoyl chloride was added to 50 ml of methylene dichloride. Then, 1.8 g (0.025 mol) of 2-butyn-1-ol was added dropwise as well as 2.6 g of triethylamine in 10 ml of methylene = chloride. The reaction product was stirred at room temperature overnight, washed twice with water and dried over magnesium sulfate, resulting in 4.0 g of product.

Example 20

O CH2-CH-CHg n = c-s-ch2-c-n ^^ CH2-CH * CH2 9.7 g (0.1 mole) of potassium thiocyanate was dissolved in 100 ml of acetone. Then, 8.7 g (0.05 mol) of Ν, Ν-diallyl chloroacetamide was added at room temperature along with 10 ml of dimethylformamide. The reaction product was stirred overnight and then partially stripped. Water was added with two portions of 100 ml of ether. The ether was separated, dried and stripped to yield 7.2 g of product.

Example 21.

-

CHCl 2-NH-C-O

\ CB2

A solution of benzene containing 50 g of 7.4 g (0.05 mole) of dichloroacetyl chloride was formed. To this solution, 3.0 g (0.05 mole) of cyclopropylamine and 5.2 g of triethylamine in 2 ml of benzene were added at a temperature of 5-10 ° C. A precipitate was obtained and the mixture was stirred for 2 hours at room temperature and for 1 hour at 50-55 ° C. The product was worked up as in the previous examples, resulting in 5.7 g of product.

Example 22.

o 163583 O y —- v CHCl2-C-ilK-CH2-V \ -o

To 4.7 g (0.032 mol) of piperonylamine and 1.2 g of sodium hydroxide in 30 ml of methylene chloride and 12 ml of water was added 4.4 g (0.03 mol) of dichloroacetyl chloride in 15 ml of methylene chloride at -5 to 0 ° C. The mixture was further stirred for 10 minutes at ca. 0 ° C and then allowed to warm to room temperature with stirring. The layers were separated and the organic layer was washed with dilute hydrochloric acid, 10% sodium carbonate solution, water and dried to give 5.9 g of product.

Example 23

0 .CH -CH-CH, ξ VcH = CH-C - «/ X CHp-CH = CH0 Cl * Δ

A solution of 75 ml of benzene containing 5.7 g of methachlorocinnamyl chloride was formed. To this solution, 3.2 g of diallyl = amine and 3.3 g of triethylamine in 2 ml of benzene were added at a temperature of 5-10 ° C. A precipitate was formed and the mixture was stirred for 2 hours at room temperature and for 1 hour at 55 ° C. The product was washed and worked up, resulting in 5.8 g of product.

Example 24.

(CHC10-C-N) -CH- CH3 3

A 500 cm 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then, 11.9 g of 2,4-dimethylpiperidine, 4.0 g of sodium hydroxide solution and 100 ml of methylene chloride were charged to the flask and the mixture was cooled in a dry ice-acetone bath. Then, 14.7 g (0.10 mol) of dichloroacetyl chloride was added portionwise. The mixture was stirred for 1 hour and immersed in an ice bath and then separated, the lower organic phase being washed with two portions of 100 ml of dilute hydrochloric acid and two portions of 100 ml of 5% sodium carbonate solution, dried over magnesium sulfate and evaporated in a rotary evaporator under water pump vacuum, resulting in 19.3 g of product.

Example 25

CHCl2-C-N}

A 500 ml 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then, 14.6 g (0.105 mole) of cis-trans-decahydroquinoline and 4.0 g of sodium hydroxide solution and 100 ml of methylene chloride were added together. Then, 14.7 g of dichloroacetyl chloride was added portionwise. The reaction mixture was worked up by stirring for ca. 1 hour, immersed in an ice bath and then phase separated, washing the lower organic phase with two portions of 100 ml of dilute hydrochloric acid, two portions of 100 ml of 5% sodium carbonate, dried over magnesium sulfate and evaporated to give 22.3 g of product.

Example 26. 0 o ch 2 -ch 2 -ch 2 -nh-c-chci 2 chci 2 -c-n / 2

A 500 ml 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then, 13.6 g (0.104 mol) of 3,3'-iminobis-propylamine were added together with 12.0 g of sodium hydroxide solution and 150 ml of methylene chloride. Then the mixture was cooled in a dry ice-acetone bath and 44.4 g (0.300 mole) of dichloroacetyl chloride were added portionwise. An oily product was formed which was not soluble in methylene chloride but separated and washed with two portions of 100 ml of dilute hydrochloric acid and allowed to stand overnight. The next morning, the product was washed with two portions of 100 ml of 5% sodium carbonate solution and the product dissolved in 100 ml of ethanol and dried over magnesium sulfate, resulting in 21.0 g of product.

143583 12

Example 27

O CH - L. n J

il S '^^ CHCl ~ -C-N ^ NC3H7-n

A 500 ml 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then 7.5 g of tetrahydrofurfuryl-n-propyl = amine (0.0525 mol) and 2.0 g of sodium hydroxide solution and 100 ml of methylene chloride were added therein. Then 7.4 g (0.05 mol) of dichloroacetyl = chloride was added. The mixture was stirred for an additional 1 hour in an ice bath and then separated, washing the lower organic phase with two portions of 100 ml of dilute hydrochloric acid and two portions of 100 ml of 5% sodium carbonate solution, dried over magnesium sulfate and evaporated, 12.7 g of product.

Example 28.

"Γ \ CHC12-C-N i

Example 27 was repeated in its entirety except that 8.9 g of piperidine was used as amine.

Example 29.

2 / - \

CHC1 - C-N O

2 w

Example 28 was substantially replicated in its entirety except that 9.1 g of morpholine was used as amine.

Example 30.

O nh-c-chci2

CHC1 - C-NH-CH

NQ

3.2 g of benzaldehyde and 7.7 g of dichloroacetamide were combined with 100 ml of benzene and ca. 0.05 g of paratoluene sulfonic acid. The mixture was heated at reflux until water transition ceased.

On cooling, the product crystallized from benzene, resulting in 7.0 g of product.

Example 31.

Φϊ Fs

- C-NH-C-GsCH

2.5 g of 3-amino-3-methylbutyn was dissolved in 50 ml of acetone, and 3.5 g of triethylamine was added followed by 6.0 g of adamantane'-1-carbonyl chloride, which was added dropwise with stirring and cooling. . The mixture was poured into water and the solid product was isolated by filtration and dried under vacuum, resulting in 6.5 g of product.

Example 32.

CH3 O N = CC-NH-C v CH3 ry-c-nh-cc = n CH O w / i 3 ri o -C-NH-C ^ ch3 5.1 g of 2-cyanoisopropylamine was dissolved in 50 ml of acetone added 6.5 g of triethylamine, followed by 5.3 g of benzene-1,3,5-tricarboxylic acid chloride, which was added dropwise with stirring and cooling. The mixture was poured into water and the solid product was isolated by filtration and dried under vacuum, resulting in 7.6 g of product.

Example 33

14 1435 $ 3

ISLAND

C-N (CH2-CH = CH2) 2

I CHJ

CN (CH 2 -CH = CH 2) 2.0 g of diallylamine was dissolved in 50 ml of methylene chloride, 6.5 g of triethylamine was added and 6.6 g of 3,6-endomethylene-1,2,3,6-tetra = hydrophthaloyl chloride was added dropwise with stirring and cooling. When the reaction was complete, the mixture was washed with water, dried over magnesium sulfate and stripped under vacuum, resulting in 9.3 g of product.

Example 34.

-. O CH 2 -CH = CHO -CH-CH-CN 2 XCH 2 2 CH 2 CH-CH 3 4.0 g of diallylamine was dissolved in 50 ml of methylene chloride, 4.5 g of triethylamine was added and 7.2 g of trans phenylcyclopropanecarbonyl = chloride was added dropwise with cooling and stirring. When the reaction was complete, the mixture was washed with water, dried over magnesium sulfate and stripped under vacuum, resulting in 9.3 g of product.

Example 35.

.q

CHC1 - N-C

X "ch2

A solution of 4.0 g (0.03 mole) of 2-methyl = indoline, 7.0 ml of triethylamine and 100 ml of methylene chloride was formed. Then, 2.9 ml of dichloroacetyl chloride was added over about a. 1 minute under dry ice cooling, keeping the temperature below 0 ° C. The solution was allowed to warm to room temperature and allowed to stand for 1 hour, after which it was washed with water and then with dilute hydrochloric acid, dried over magnesium sulfate and evaporated to give a solid which was washed with n-pentane to obtaining 5.0 g of product.

Example 36.

? / C3H7'n CHLCI-C-In Ό 3

A 500 cm 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then, 8.9 g of cyclooctyl-n-propylamine, 2.0 g of sodium hydroxide solution and 100 ml of methylene chloride were charged to the flask and the mixture was cooled in a dry ice-acetone bath. Then 5.6 g of chloroacetyl chloride was added portionwise. The mixture was stirred for a further ca. 1 hour, immersed in the ice bath and then phase separated, whereupon the lower organic phase was washed with two portions of 100 ml of dilute hydrochloric acid and two portions of 100 ml of 5% sodium carbonate = solution, dried over magnesium sulfate and evaporated, resulting in 9.5 g of product.

Example 37.

n / C2H5 ch2ci-c-nC "π-λ ^ CH2 ~ \ J / ~ CH

A 500 cm 4-neck flask was provided with a stirrer, thermometer and drip funnel. Then, 7.8 g (0.0525 mol) of p-methylbenzyl = ethylamine, 2.0 g of sodium hydroxide solution and 100 ml of methylene chloride were charged to the flask. The mixture was cooled in a dry ice-acetone bath. Then 5.6 g (0.05 mole) of chloroacetyl chloride was added portionwise. The mixture was stirred for a further ca. 1 hour, immersed in the ice bath and then phase separated, after which the lower organic phase was washed with two portions of 100 ml of dilute hydrochloric acid and then two portions of 100 ml of 5% sodium carbonate solution, dried over magnesium = evaporated to give 9.5 g product.

Example 38

"-O

CHC12-C-NH-L ^ N

4.7 g of aminopyridine was charged to a reaction vessel with 100 ml of acetone and stirred at 10-15 ° C. Then, 7.0 ml of triethyl = amine was added dropwise. Then 5.25 ml of dichloroacetyl chloride in 10 ml of acetone was added over 5 minutes and stirred at room temperature. The solid was filtered off and washed with acetone, resulting in 10.0 g of product.

Example 39

ISLAND

S

II

8.1 g (0.05 mole) of 4-aminophthalimide was dissolved in 100 ml of dimethyl = furan and 5.0 g of dichloroacetyl chloride was then added with stirring at 0-10 ° C over 5 minutes. Then 7.0 ml of triethylamine was added. The reaction mass was stirred for 1 1/2 hours at room temperature and then 1 liter of water was added. The reaction mass was filtered, washed with water and dried, resulting in 12.0 g of product.

Example 40. O

O> CH2-CH2-O-C-NH-C3H7-i chCl2-c-n ^^ CH2-CH2-O-C-NH-C3H7-i

ISLAND

In this example, the compound was prepared by reaction of 5.4 g of N, N-bis (2-hydroxyethyl) dichloroacetamide with 4.3 g of isopropyl = isocyanate in 50 ml of acetone in the presence of dibutyltin dilaurate and triethylenediamine catalysts, resulting in 8 , 2 g of product.

Example 41. 0 __ o .ch2-ch2 ~ o-c-nh-Y s \ ch2ci-c-n ^ -.

^ ch2-ch2-o-c-nh— {s y

In this example, the compound was prepared by reacting 3.6 g of N, N-bis (2-hydroxyethyl) chloroacetamide with 5.0 g of cyclohexyl = isocyanate in the presence of 50 ml of acetone and dibutyltin dilaurate and triethylenediamine catalysts. The reaction mass was heated at reflux and stripped under vacuum, resulting in 6.9 g of product.

Example 42

0

CHC12-C-I ^ I

15 g of acetone and 12.2 g of ethanolamine were combined in 150 ml of benzene and heated at reflux until the passage of additional water ceased. The resulting solution was examined and found to contain 2,2-dimethyl-1,3-oxazolidine. One quarter of the benzene solution (0.05 mole) was reacted with 7.4 g of dichloroacetyl chloride and 5.5 g of triethylamine, washed with water, dried and stripped under vacuum, resulting in a light golden brown solid. A portion was recrystallized from ether to give a white product.

Other compounds were prepared in an analogous manner by starting from appropriate starting materials as indicated above. The following table lists a number of compounds representative of those used in the invention. The connections are each assigned a number and these numbers are used for identification throughout the rest of the description.

18 143583 f S ΐ

and I U O K

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k æ κ cn 0 CJ co S3

1 I U O

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and cg cm ffi U oj U

æ æ n n- 's 0 u o u u o u

i-ι cg I I l I i I · I

Pi Pi H \ /

I-I S

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too coiUU nh cg cg cg cg H H

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1 I I I I I I I I I I I I I I

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X sx β o te 143583 19 sc υ

III

ri ro ro

γ in «SC

CM I æ = aT Γο = u-O = 1—1 ^ «I S y l_Y ογδ W ^ Zf υ sf 1 l u 1 sc u u sc I u

CM II

H I -. ro sc .--. ellcosSCUSCs = = = = = =

+ J SC U I

cd u I cm m ^ sc +> u u

Μ I I

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H

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firHiHiH | H CM rM CM CM CM CM CM CM

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cm I II κι ro i SB <o l SB co

Pi 2 M S3 Si U CM SB CM U SB CM CJ SB

-aom-OB'-O sb u ~ u ss ~ u sb - I 1 u i u i ο α i u u

I I II II

CM CM CM

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o u o

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τα Arrow I cm cm 'cm I

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co co σι σ co BOBKO m u i ^ i SB “cm U U -

CM CM SB -—- I I CO

CM H O u <o -P -P SB

pit H a I I SB I I Ό O SB O = CM u CM CM = =

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H

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£ CM CM CMCOCOCOCOCOCOCOCOCO

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P

0

Pm 143583 21 a a a a a o a ΰ u u a u g y

I "I I πΓ i I i" i I aT

o u u u u y 111 u y i u u

~ y I II I II y I h - cn II

cn i co n cn a cn a l cn a m - a «ib a y a co y uu = co I CO i a ms» y a i - cn a cm a cn y a cn ^ y cn aa y a u a - y a a ~ a

y U ~ y - y B ~ U UUU

II UIOIUU 1111

I I II

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cn cn a a a n a a u u cn u, -. h i a u a ii ii a ii 4-1 Ph o ii ii a co a u a

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The agent of the invention was tested as follows.

Sample 1; Jordindarbejdning

Small flat plant boxes were filled with Felton's clay-mixed sandy soil. The herbicide and herbicide antidote were applied separately or in combination on the ground as it was mixed in a 20 liter cement mixer. The following stock solutions were prepared from each compound when the herbicide and antidote were applied separately. A stock solution of the herbicide was prepared by diluting 1 g of a concentrate of the herbicide with 100 ml of water. Of the antidote, 70Q mg of technical material was diluted with 100 ml of acetone. 1 ml of these stock solutions is equivalent to 7 mg of active ingredient or 1 kg per ml. hectares when the treated land is placed in 20 x 30 x 7.5 cm plant boxes. After the soil was treated with the herbicide and antidote in the desired amounts, the soil was transferred from the cement mixer to 20 x 30 x 7.5 cm plant boxes where it was now ready for sowing maize seeds. A 1/2 liter soil sample was then removed from each plant box and stored to cover the seeds after sowing. The earth was planned and rendered with a depth of approx. 1 cm was formed in each plant box. A sufficient number of seeds were sown to obtain good plants at each treatment. The seeds were then covered with the half liter of soil that had been removed immediately before sowing.

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143583 79

Sample 2: Corn Seed Treatment.

Small flat plant boxes were filled with Felton's clay-mixed sandy soil. Soil containing herbicides were used this time. The soil from each plant box was placed in a 20 liter cement mixer where the soil was mixed as the herbicides were applied as a stock solution in 100 ml of water. The stock solution was prepared by diluting 1 g of a herbicide concentrate.

1 ml stock solution was added to the soil from one volumetric pipette per ml. 0.454 kg of the desired herbicide. 1 ml stock contains 7 mg of herbicide equal to 1 kg per day. hectares when the treated land is placed in 20 x 30 x 7.5 cm plant boxes. After the herbicide mixture, the soil was again placed in the plant boxes.

Plant boxes with herbicide treated and untreated soil were then ready to be sown. A 1/2 liter soil sample was then removed from each plant box and stored to cover the seeds after sowing. The earth was planned and rendered with a depth of approx. 1 cm was formed for sowing the seeds. Rows with treated and untreated crop seeds were alternately sown. At each sample, six or more seeds were sown in each gutter. The gutters were formed with a spacing of approx. 4 cm in the plant box. The seed treatment was done by placing 50 mg of the seed treatment compound together with 10 g of seeds in a suitable container and shaking them until the seeds were uniformly covered with the seed treating agent. The seed treatment compounds were applied as liquid slurries and by powder or powder treatments. In some cases, acetone was used to dissolve powdered or solid compounds so that they could be applied more effectively to the seeds.

After sowing the seed boxes, they were covered with half a liter of soil that had been removed immediately before sowing. The seed boxes were placed on greenhouse benches where the temperature was 21-32 ° C. The seed boxes were irrigated by sprinkling as needed to ensure good plant growth. Percentage damage assessments were made 2 to 4 weeks after the treatments were performed.

143563 80

For each sample, the herbicide is applied alone or in combination with the seed protection agent, and the seed protection agent is applied alone to control phytotoxicity. The results of these tests are given in the following Table III.

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The antidote compound of the agent of the invention can be used in any convenient form. Thus, the antidote may be included in emulsifiable liquids, emulsifiable concentrates, liquids, wettable powders or granules or any other form. In the preferred form, the antidote compound is mixed with the thiol carbamates and incorporated into the soil before or after sowing the seeds. However, it is to be understood that the thiol carbamate herbicide can be incorporated into the soil and that the antidote compound can then be incorporated into the soil. Furthermore, seeds can be treated with the antidote and sown in the soil which has been treated with the herbicide or has not been treated with the herbicide but is then treated with herbicide. The method of adding the antidote does not affect the herbicidal activity of the carbamate compounds.

The amount of antidote present is approx.

0.0001-30 parts by weight per part by weight thiol carbamate herbicide. The exact amount of antidote compound will usually be determined by economic conditions with respect to the most effective amount used.

In the following claims, the term "active herbicide compound" encompasses the active thiol carbamates. Furthermore, the active herbicidal compound is different from the antidote compound.

The herbicidal compounds used in the method of the invention are effective herbicides whose herbicidal activity varies among the various compounds and among the combinations of different compounds. Similarly, the degree of activity varies to some extent with the plant species applied to a particular combination. Thus, a particular herbicide compound or combination of herbicidal compounds can be readily selected to control undesirable plant species.

By means of the method and agent according to the invention, prevention of damage to a desired crop species can be achieved by using a particular compound or combination.

Claims (2)

The herbicidal compounds used in the method of the invention are active herbicides of a common type. That is, they are herbicidal effective against a wide variety of plant species without discrimination between desirable and undesirable species. The method of controlling vegetation involves applying a herbicidal effective amount of the previously described herbicidal compounds to the area or plant site where control is desired. A herbicide used here is a compound that controls or modifies the growth of vegetation or plants. Such control or modification effects include all deviations from natural evolution, e.g. killing, retarding, decaying, desiccation, regulation, crippling, vanishing, stimulation, dwarf growth and the like. By "plants" is meant germinating seeds, emerging seedlings and established vegetation comprising roots and parts above ground. The herbicides listed in the tables are used in amounts which lead to effective control of undesirable vegetation. The quantities are within the quantities recommended by the supplier. Therefore, in each case weed control is commercially acceptable within the desired quantities. Claims. 1. A method for controlling weeds, characterized in that a herbicidal effective amount of thiocarbamate of the general formula is therefore applied at the growing site Wherein R1 is an alkyl group of 1-6 carbon atoms, a chloro = benzyl group or a haloalkenyl group of 2-4 carbon atoms, and R and R which may be the same or different, al = cooling groups having 1-6 carbon atoms or cycloalkyl groups having 3-6 1 '2' carbon atoms, or wherein R and R together with the nitrogen atom to which they are attached form a ring of 4-7 carbon atoms as herbicide active compound, and that on the growing site or on the seeds per. part by weight of active herbicide compound is added to 0.0001-30 parts by weight of an antidote, therefore, of the general formula O / R1 rcn / R2 wherein R belongs to the group comprising haloalkyl, haloalkenyl, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, halogen, hydrogen, carbalkoxy, N-alkenylcarbamylalkyl, N-alkynylcarbamylalkyl, N-alkenylcarbamyl, N-alkyl-N-alkynylcarbamyl, N-alkynylcarbamyl, N-alkyl-N-alkynylcarbamylalkyl, N-alkenylcarbamylalkoxyalkyl, N-alkenylcarbamyl alkyl-N-alkynylcarbamylalkoxyalkyl, alkynyloxy, haloalkoxy, alkylthio = cyanatoalkyl, alkenylaminoalkyl, alkylcarbonylalkyl, cyanoalkyl, cyanatoalkyl, alkenylaminosulfonalkyl, alkylthioalkyl, halo = alkylcarbonyloxyalkyl, carbalkoxy, halogenalkenylcarbonyl = oxyalkyl, hydroxyhalogenalkyloxyalkyl, hydroxyalkylcarbalkoxy = alkyl, hydroxyalkyl, alkoxysulfonalkyl, furyl, thienyl, alkyl di = thiolenyl, thienalkyl, phenyl and diphenylalkyl, wherein the cycloalkyl = groups and alkoxy groups and alkyl the groups which may be straight or branched contain 1-20 carbon atoms and the alkenyl and alkynyl groups are straight or branched and contain 2-20 carbon atoms, preferably 2-12 carbon atoms; substituted phenyl wherein the substituents may be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, N-alkenylcarbamyl, N-cyanoalkylcarbamyl, nitro, carboxyl and carboxylate and haloalkylcarboxamido, and N-alkenylcarbamylcycloalkenyl; phenyl = alkyl, phenylhaloalkyl and phenylalkenyl, the alkoxy groups and alkyl groups containing 1-2 carbon atoms and the alkenyl groups containing 2-3 carbon atoms; and substituted phenylalke = 118 t43583 aminocarbonyl, wherein the substituents may be selected from halogen, alkyl and alkoxyf halophenoxy, phenylalkoxy, phenylalkylcarboxyalkyl, phenylcykloalkyl, halophenylalkenoxy, halogenphenylthioalkyl, halophenoxyalkyl, bicycloalkyl, alkenylcarbamylpyridinyl, alkyl kynylcarbamylpyridiny1, dialkenylcarbamylbicykloalkenyl and al = kynylcarbamylbicykloalkenyl wherein cykloalkylgrupperne and the cyclo = alkenyl groups contain 3-20 carbon atoms and the alkyl groups contain 1-2 carbon atoms, the alkenyl groups contain 2-3 carbon atoms, and the alkynyl groups contain 2-3 carbon atoms, 1 2 R and R are the same or different and belong to the group comprising alkenyl, haloalkenyl, hydrogen , alkyl, haloalkyl, halogenesulfonyl, alkynyl, cyanoalkyl, hydroxyalkyl, hydroxyhalogen = alkyl, haloalkylcarboxyalkyl, alkylcarboxyalkyl, alkoxycarboxyalkyl, alkylmercaptocarboxyalkyl, carbalkoxyalkyl, alkylcarbylamyloxyalkyl, amino, amino mido, halogen = alkylamido, haloalkylamidoalkyl, haloalkyl-N-alkylamidoal = alkyl, haloalkylamidoalkenyl, alkylideneamino, cycloalkyl, alkyl-cycloalkyl, alkoxyalkyl, alkansulfonyloxyalkyl, mercaptoalkyl, alkylaminoalkyl, carbalkoxyalkenyl, haloalkylcarbonyl, alkyl = carbonyl, alkenylcarbamyloxyalkyl, cykloalkylcarbamyloxyalkyl, alkoxycarbony1, haloalkoxycarbonyl, halogenophenylcarbamyloxy = alkyl, cycloalkenyl and phenyl wherein the cycloalkyl groups and the alkoxy groups, as well as the alkyl groups which may be straight or branched, contain 1-20 carbon atoms and the alkenyl and alkylene groups are straight or branched and contain 2-20 carbon atoms, preferably 2 -12 carbon atoms \ substituted phenyl wherein the substituents may be selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido, phthalamidyl, hydroxy, alkylcarbamyloxy, alkenylcarbamyloxy, alkylamido, haloalkylamido and alkylcarbonylalkenyl; benzenesulfonyl and phenylalkyl, the alkoxy groups containing 1-2 carbon atoms, the alkyl groups containing 1-3 carbon atoms, and the alkenyl groups containing 2-3 carbon atoms and substituted phenylalkyl, wherein the substituents may be selected from halogen, alkyl, alkylenedioxy and halogenophenoxyalkylamidoalkyl; alkylthiadiazolyl, piperidylalkyl, thiazolyl, alkylthiazolyl, benzothiazolyl, halogenobenzothiazolyl, furylalkylpyridyl, alkylpyridyl, alkylpiperidyl, alkylisoxazolyl, tertrahydr ofurylalkyl, 3-cyano-4-, 5-alkylentylienyl, -haloalkylacetamidohalogenphenylalkyl and cyanoalkenyl, wherein the alkyl groups contain 1-3 carbon atoms and the alkenyl groups 12 contain 2-3 carbon atoms or where R and R together with the nitrogen atom to which they are attached form the group = pyridinyl, alkylpiperidinyl, alkyltetrahydropyridyl, morpholyl, alkylmorpholyl, azabicyclononyl, benzoalkylpyrrolidinyl, oxa = zolidinyl, alkyloxazolidinyl, perhydroquinolyl, alkylperhydro5 = quinolyl or alkylaminoalkenyl, wherein the alkyl groups and alkenes are from 2 and the alken = 2 nyl group . An agent for carrying out the process according to claim 1, characterized in that it comprises thiocarbamate of the general formula O / R1 'R'-SCN 2' wherein R 'represents an alkyl group of 1-6 carbon atoms, a chlorobenzyl group or a haloalkenyl group having 2-4 carbon atoms, 1 '2' and R and R, which may be the same or different, means alkyl groups having 1-6 carbon atoms or cycloalkyl groups having 3-6 1 '2' carbon atoms, or wherein R and R together with the nitrogen atom to which they are attached form a ring of 4-7 carbon atoms as herbicidal active compound, as well as by weight of active herbicide compound 0.0001-30 parts by weight of an antidote, therefore, of the general formula 0 yR1 RCn 'Xr2 wherein R belongs to the group comprising haloalkyl, haloalkyl, nyl, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, halogen, hydrogen, carbalkoxy, N-alkenylcarbamylalkyl, N-alkynylcarbamyl = alkyl, N-alkenylcarbamyl, N-alkyl-N-alkynylcarbamyl, N-alkylcarbamyl, N-alkyl-N-alkynylcarbamylalkyl, N-alkenylcarbamylalkoxyalkyl, N-alkenylcarbamyl N-alkynylcarbamylphenyl, 143583 120 N-alkyl-N-alkynylcarbamylalkoxyalkyl, alkynyloxy, haloalkoxy, thiocyanatoalkyl, alkenylaminoalkyl, alkylcarbonylalkyl, cyano, = alkyl, cyanatoalkyi, alkenylaminosulfonalkyl, alkylthioalkyl, haloalkylcarbonyloxyalkyl, carbalkoxy, haloalkenyl * carbonyloxyalkyl, hydroxyhalogenalkyloxyalkyl, hydroxyalkyl * carbalkoxy, hydroxyalkyl, alkoxy sulfonalkyl, furyl, thienyl, alkyl dithiolenyl, thienalkyl, phenyl and diphenylalkyl wherein the cycloalkyl groups and the alkoxy groups together the alkyl groups, which may be straight or branched, contain 1-20 carbon atoms and the alkenyl and alkynyl groups are straight or branched and contain 2-20 carbon atoms, preferably 2-12 carbon atoms; substituted phenyl wherein the substituents may be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, N-alkenylcarbamyl, N-cyanoalkylcarbamyl, nitro, carboxyl and carboxylate and halogenoalkylcarboxamido, and N-alkenylcarbamylcycloalkenyl; phenylalkyl, phenylhaloalkyl and phenylalkenyl, the alkoxy and alkyl groups containing 1-2 carbon atoms and the alkenyl groups containing 2-3 carbon atoms; and substituted phenylalkenyl, wherein the substituents may be selected from halogen, alkyl and alkoxy; halophenoxy, phenylalkoxy, phenylalkylcarboxyalkyl, phenyl, cycloalkyl *, halophenylalkenoxy, halogenphenylthioalkyl, halo * genphenoxyalkyl, bicycloalkyl, alkenylcarbamylpyridinyl, alkyl * nylcarbamylpyridinyl, dialkenylcarbamylbicykloalkenyl and alkynyl * carbamylbicykloalkenyl wherein cykloalkylgrupperne and cykloalke * nylgrupperne contains 3-20 carbon atoms and the alkyl groups contain 1-2 carbon atoms, the alkenyl groups contain 2-3 carbon atoms and the alkynyl groups contain 2-3 carbon atoms, 12 R and R are the same or different and belong to the group comprising alkenyl, haloalkenyl, hydrogen, alkyl, haloalkyl, halo * sulfonyl, alkynyl, cyanoalkyl, hydroxyalkyl, hydroxyhaloalkyl , haloalkylcarboxyalkyl, alkylcarboxyalkyl, alkoxycarboxyalkyl, alkylmercaptocarboxyalkyl, carbalkoxyalkyl, alkylcarbamyloxyalkyl, amino, formyl, haloalkyl-N-alkylamido, haloalkylamino, haloalkylamidoalkyl, haloalkylamyl-N cycloalkyl, alkylcycloalkyl, alkoxyalkyl, alkanesulfonyloxyalkyl, mercaptoalkyl, alkylaminoalkyl, carbalkoxyalkenyl, haloalkylcarbonyl, alkyl * carbonyl, alkenylcarbamyloxyalkyl, cycloalkylcarbamyloxyalkyl,