CS259274B1 - 3-Aryloxy-acetyl-2-benzothiazolinenes and a process for their preparation - Google Patents

Abstract

The solution relates to 3-aryloxyacetyl-2-benzothiazolinones of general formula I 0 \ \ N~CQ~C.lhO / Rn íi) in which R is methyl, chlorine and n is an integer 0-3 or Rn is a fused benzene ring, and a method for preparing compounds of general formula I consisting of acylation of 2- -benzothiazolinone with aryloxyacetic acid chlorides in the presence of a base at temperatures of 40-80 ° C. The prepared compounds are characterized by herbicidal and growth-regulatory effects.

Description

239274

The invention relates to 3- (aryloxyacetyl) -2-benzothiazolinones and to a process for their preparation. The compounds have herbicidal and growth regulatory effects.

It is known that in agricultural practice they use plant protection agents in which benzothiazole derivatives such as N- (2-benzothiazol-1-yl) -N'-methylurea (benzothiazuronj, N - (2- benzothiazolyl) -N, N'-dimethylurea (metabenzothiazuron) The 3-haloalkyl, 3-alkyl or 3-acetyl derivatives of 2-benzothiazolone exhibit a broad spectrum of biological activity, namely herbicidal, morpholytic and fungicidal effects (D 'Amico, JJ' Eur. Pat. Appl. 2 932; Bindler, J., Mo del, E .: Ger. 1 023 627; D 'Amico, JJ: USApat. 4 187 098; D' Amico, JJ: U.S. Pat. No. 5,676,512, U.S. Pat.

6-bromo-3- (aryloxyacetyl) -2-benzothiazolinones are also known to have herbicidal properties (Lácová M., Sidóová, E., Konečný, V .: Cs. Aut. No. 246 247 ). It is known that the starting 2-benzothiazolinone is ineffective in herbicide. Furthermore, aryloxyacetic acids are also known to have practical application in plant protection as herbicides.

3- (aryloxyacetyl) -2-benzothiazolinones of formula I have now been found

N ~ CO

Chh11) wherein R is chloro, methyl and n is an integer from 0 to 3 or Rn forms a fused benzene core. Simultaneously, the production of compounds of formula I by acylation of 2-benzothiazolinone with aryloxyacetic acid chlorides at a temperature of about 40-80 ° C was observed in the presence of a base. In the compounds of formula I, the herbicidal and racemic-regulating effects found at the same time were comparable to the standard: 2-methyl-4-chlorophenoxyacetic acid, for example 3- (4-chlorophenoxyacetyl) -2-benzothiazolinone at 100% inhibited plant preemergence: Sinaplsalba, Amaranthus retroflexus, Linum usita-tissimum at 5 kg / ha, and 1.58 kg / ha and 3.16kg / ha at post-emergence application.

The following examples illustrate but do not limit the invention. Example 1 3-Phenoxyacetyl-2-benzothiazolinone

A mixture of 2-benzothiazolinone (50 mmol) of phenoxyacetic acid chloride (55 mmole) and dimethylformamide (20 cm 3) was heated to 40-60 degrees Celsius for 10 minutes then cooled and added with stirring while stirring. pyridine (60 mmol). After the addition, the reaction was heated to 40-60 ° C and stirred for 1-3 h. Thereafter, it was added to the reaction mixture. The precipitated white precipitate is filtered off with suction, washed with sodium bicarbonate solution (5%) and recrystallized from ethanol. The melting point for Example 1 is 112-114 ° C.

H, 3.89; N, 4.91; N, 11.29. Found: C, 63.43; H, 3.86; 99% N, 11.46% S. EXAMPLE 2 3- (4-Chlorophenoxyacetyl) -2-benzothiaziazone

Procedure as in Example 1.

Reactants: 2-benzothiazolinone, 4-chlorophenoxyacetic acid chloride, base: pyridine or triethylamine, crystallized from acetone or acetic acid. Melting point: 148-149 ° C.

H, 3.15; N, 4.38; N, 10.03; Cl, 11.09. Found: C, 56.13; H, 3.48%. N, 4.25% N, 10.78% Cl, 9.82% S. Example 3 3- (2,4,5-Trichlorophenoxyacetyl) -2-benzothiazolone

Procedure as in Example 1.

The reactants are: 2-benozthiazolinone, 2,4,5-trichlorophenoxyacetic acid chloride. The temperature of the product is 192-194 ° C.

% C, 46.37;% H, 2.07; N, 3.60; S, 26.80; Cl, Found: 46.22. % N, 3.48%, 8.56%, 26.80% Cl. 259274 Example 4 3- (2-Naphtyloxyacetyl) -2-benzothiazolinone

Procedure as in Example 1.

The reactants are: 2-benzothiazolinone, 2-naphthyloxyacetic acid chloride. The melting point of the product is 168-170 ° C.

H, 3.91; N, 4.18. Found: C, 68.18; H, 4.01; 4.14% N, 9.37% S. Example 5 3- (3-Methylphenoxyacetyl) -2-benzothiazolinone

Procedure as in Example 1.

The reactans are: 2-benzothiazolinone, 3-methylphenoxyacetic acid chloride. The melting point of the product is 109-110 ° C.

H, 4.38; N, 4.68; N, 10.70; S, 64.35; C, 4.21; H, 4; Example 6 3- (2-Methyl-4-chlorophenoxyacetyl) -2-benzothiazolinone

Procedure as in Example 1.

The reactants are: 2-benzothiazolinone, 2-methyl-4-chlorophenoxyacetic acid chloride. Melting point of the product is 145-148 ° C. Analysis for C 16 H 12 ClNO 3 S (333) calculated: 57.65% C, 3.60% H, 4.20% N, 9.61% S, 10.66% Cl, found * 57, H, 4.43; N, 9.61; Cl, 10.91. Example 7

The herbicidal activity of the compounds of the invention.

Sample 1: 3- (4-chlorophenoxyacetyl) -2-benzothiazolone,

Sample 2: 3- (2,4,5-Trichlorophenoxyacetyl) -2-benzothiazolone,

Standard: 2-methyl-4-chlorophenoxyacetic acid (MCPA)

Table 1 Activity of substances in pre-emergence application on four species of test plants

Plants: Dose Sample 1 Sample 2 Standard

Avena sativa A

B

Fagopyrum vulgare A

B

Sinapis alba A

B

Lepidium sativum A

B Batch A == conc. 15 kg / ha; dose— = not tested 3 3- 0 0 5 5 5- 5 5 5 5 5 - 5 5 5 5 5- 5 5 5 - conc. 5 kg / ha

The pre-emergence application is carried out by spraying the aqueous emulsion of the substances in said doses directly on the stage in front of the outlet. Experiments were carried out in greenhouse conditions. The vaccine was visually assessed after the damage was eliminated by means of a 0—5 scoreboard, 0 being plant-damaged and 5 being dead. 1 - 4 damage limits.

Claims (2)

3-Aryloxyacetyl-2-benzothiazolinones of the general formula I wherein v. / vy lit R is methyl, chloro and n is an integer of 0 to 3, or R 11 can be a fused benzene ring. 2. A process for the preparation of compounds of the formula I which is acylated with 2-benzothiazolinone with aryloxyacetic acid chlorides in the presence of a base at temperatures of 40-80 [deg.] C.