SU725541A1 - Herbicidic agent - Google Patents

Abstract

1. A diurethane of the general formula see diagramm : EP0000030,P50,F6 where Z denotes the radical see diagramm : EP0000030,P50,F7 and Y denotes the radical see diagramm : EP0000030,P50,F8 Z always being different from Y and R**1 and R**2 being identical or different and each denoting hydrogen, alkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, alkoxycarbonylalkyl of 3 to 5 carbon atoms, haloalkyl of 1 to 4 carbon atoms, unsubstituted benzyl, or benzyl substituted by alkyl of 1 to 4 carbon atoms or halogen, R**3 and R**4 being identical or different and each denoting unsubstituted alkyl of 1 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, alkoxy of 1 to 2 carbon atoms, halogen-substituted phenyl or unsubstituted phenyl, alkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, unsubstituted or C1 -C4 -alkyl- substituted cycloalkyl of 5 to 8 carbon atoms, bicycloalkyl of 7 to 8 carbon atoms, tricycloalkyl of 10 to 15 carbon atoms, phenyl with a fused ring system, phenyl or mono- or poly-substituted phenyl with the substituents alkyl of 1 to 4 carbon atoms, halogen or alkoxy of 1 to 3 carbon atoms, X denotes hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 or 2 carbon atoms, halogen, nitro or amino, n denotes one of the integers 1, 2, 3 and 4, and A, B, D and E are identical or different and each denotes oxygen or sulfur (with the proviso that the radicals A, B, D and E are not simultaneously oxygen and one of the radicals always denotes sulfur).

Description

(54) HERBICID MEANS

one

The invention relates to chemical agents for controlling weeds and undesirable vegetation, namely, herbicidal activity containing the active substance from the group of carbamic acid derivatives, auxiliary components from the number of liquid CRX or solid carriers, surfactants, etc.

Herbnvdnye funds based on derivatives of carbamic acid are known. These include, for example, an agent based on N-carbamoyloxyphenylcarbomate esters or based on fennlen-1,3-diuretay 2.

However, the known means of this type of nedrystatio are effective in relation to individual species. Weeds or insufficiently selective in relation to cultivated plants.

The method) (1 of the invention is a new herbicidal agent based on a derivative of a carbamic acid, which has an increased herbicidal activity and a better elector: no effect.

This goal is achieved by the fact that, as the active substance of the herbinide

agents use a carbamic acid derivative of formula

Where.

210

H15

where r

hydrogen, methyl or ethnl;

 R is hydrogen, methyl, ethyl or benzyl;

R C1-C5-alkyl, cyclooctyl, methylcycloxyl, benzyl, norbornyl, phenyl, substituted phenyl, having from 1 to 3 substituents from the group Ct-C-alkyl, phtop or methoxy; R is C1-C4-alkyl, 1,1-Dimethyl-2-chloroethyl, 1,3-dimethoxyisopropyl, butyn-1-yl-3, cyclohexyl, monodi-or Trimethylcyclohexyl, treg-butylcyclohexyl or methoxycyclohexyl, hexahydrobenzyl 5-, phenyl , substituted fnil, having from 1 to 3 substituents from the number of halogens, Ci-C3, alkyl or methoxy groups, substituted by alkyl with the number of carbon atoms up to 4 phenium, tetrahydronaphthyl, 1-chloroisopropyl, adamantyl, cycloheptyl, 1-chloro-3-methoxyisopropyl , 1,3-difluoroisopropyl or 1-chlorobutyl-2; A, B, D and E - independently of each other oxygen or sulfur, and all of them cannot simultaneously mean oxygen and at least one of them always means sulfur, provided that the group Z is always different from the groups U. The content of the active substance in the herbicidal agent ranges from 0.1% by weight to 95% by weight. The method of producing compounds of general formula D is based on reacting the corresponding phenyl esters of L- (3-aminophenyl) -carbamic acid with chlorolester esters (or with tetrachloric acid chloride). They are obtained in other known ways. In tab. 1 shows compounds of general formula I and examples illustrating the effectiveness of the proposed agent of the formula V If-C-B-R V-C-D-R I, N E B Tables

725541

8 Continued table. 1 Example 1. Experiments were carried out under greenhouse conditions. In case of pre-emergence application, the preparations were treated with soil in which the seeds of experimental plants were sown. In post-emergence application, Experimental plants were subjected to treatment, and fascia under greenhouse conditions to a certain stage of development. After the treatment, the plants were grown in greenhouse conditions for another 2-4 weeks and the herbicidal activity was evaluated. Selective effect on vegetables to

Note

bristle

Continued table. 1 Rating scale: О - no effect; 100 - full of death of plants. For comparison, the known herbicides were used: A. Dioxide 3-isopropyl-2,1,3-benzothiadiazinone-4. B. MeTHn-N-13 (L – 3-methylphenylcarbamoyloxy) -phenyl Carbamate. The results of the experiments are presented in table. -18. Table 2 when used after leaving the greenhouse

3

g.

ooooaov "r) neoDO

) i:

n Г in Q О «лО« л

I e

OsOvOs O O wvO

X

yo

tft trt t

8 8 8 about about $ 5

eight,

I

8 8 8 8 8 8 8 8 8 8

i "

8888

H

i

I I §

I

  9 s

u “n rs

X

about during in about in her vO "

. 2

“Lo o“ l o. Q,

о Г1 о-н «N 4 о

X

n

S-j

. o O L Q “L Yu O Q T to

2 f

M

o o

VO

§ § I

I 2 s

eight

. 8 S M

I

R nd

° - S

mCS

"

p g "

(а 17 Selective weed control with the help of new compounds in cereals when used after germination in the greenhouse 725541. 18 Table5

0.5 2.0 0.5 2.0 0.5 2.0 0.5 2.0 Fighting broad-leaved weeds after sprouting in the greenhouse

Continued table. five

100

100 100 100

100 100 100 100 100 100 100 30 100

70 95 100 T a b litsa 6 on peanuts in the application of the Action of compounds in the application of nodie shoots in the greenhouse

Table 7

8 8 |. 8 2 and R 8 S

--1- - h-

"L

ABOUT, -.

g S i S

8 88

- 5hrs

8.88

 I-1

8 8S S S S

o booo o-o 2 ® I

oh 00 oh oh oh

th "" about about "l about LO" about about

I j o - o- - o- d S ri g

“I .:

one

8gSJ88888

88 8

OS

8 8 8 8 8 8 P

eight

00

gj l

s

Active principles with selective herbicidal action on cotton and sugar beets when processed after germination in the greenhouse

Table 10

29725541 Q

Selective control of weeds with compounds in cereals and maize when applied after sprouting in a greenhouse

0.25

1.0

2.0

1.0

0.5

1.0 Weed control in earth greenhouse

Salt control with soybean compounds when applied after sprouting in the greenhouse

Table 13

ABOUT

100

95 98

95

. 15 100 90

10 100 80 90

15

100 100

15 100 90 100

90

10,100

Table 15 Table 14 nuts when applied after germination

31,725541,32 Fight against a pair and wood lice in beets., When applied after sprouting in a greenhouse

0.5

0.25 0.5

Fight against mariya and ses1banii in m those pepper when applied after sprouting in the greenhouse Gerbschshdny action when applied after sprouting in the greenhouse

T a b l and u a 16

98 95 95

94 98 98

10 o 6

T a b, l i.ts a 17

Claims (2)

TABLE 18.33 Claims of the invention Herbic means containing carbamic acid as an active substance and auxiliary components selected from the group of liquid or solid teles, surfactants, with the aim of enhancing its activity and improving its selective action, it contains a compound of the general formula hydrogen, methyl or ethyl as a derivative of carbamic acid; hydrogen, methyl, ethyl or benzylCi-Cs-alkyl, cyclooctyl, mtyl cyclohexyl, benzyl, Morbornyl, phenyl, substituted phenyl, having from 1 to 3 substituents from 34 of the C, -C4-alkyl, fluorine or methoxy group; R C 1 -C 4 -alkyl, 1,1-dimethyl-2-chloroethyl, 1,3-dimethoxyisopropyl, BUTIN-1-IL-3, cyclohexyl, mono-, di- or trimethylcyclohexyl, 7reg-butylshylclohexyl or methoxycyclohexyl, hexahydrobenzyl, -indash 1L, phenyl, substituted phenyl, having from 1 to 3 substituents from among halogens, Ci-Cz-alkyl or methoxygroup, substituted with an alklom with up to 4 carbon atoms phenyl, tetrahydronaphthip, 1-chloroisopropyl, adamantyl, cycloheptyl, 1-chloro 3-methoxyisopr (I1Hl, 1,3-difluoroisopropyl or 1-chlorobutyl-2; A, BD and E - independently of each other or sulfur, and all of them simultaneously cannot mean oxygen, and at least one of them always means sulfur in case of acacia, that group Z is always different from the group, in an amount from 0.1 to 95 wt.%. Sources of information taken into account during the examination 1. Patent Germany N 156T151, CL. 12 O 17/01, spec 21.02.74. 2. Copyright certificate of Czechoslovakia No. 155030, 45 I 19/02, published on September 15, 74 (prototype).