SU759047A3 - Herbicidic agent - Google Patents

Abstract

1360571 S-triazine compounds MONSANTO CO 3 Jan 1972 [4 Jan 1971 24 March 1971] 70/72 Heading C2C An S-triazine of formula where Z is Cl, alkoxy or alkylthio both having a maximum of 4 carbon atoms; R<SP>1</SP> is alkyl or alkoxy alkyl both having a maximum of 8 carbon atoms; R<SP>2</SP> is alkyl having a maximum of 8 carbon atoms; R<SP>3</SP> is an unsubstituted 1- cycloalken-1-yl group or a C 1 -C 10 alkyl- or a C 1 -C 10 alkoxy-substituted 1-cycloalken-1-yl group wherein the 1-oycloalken-l-yl group has from 5 to 7 carbon atoms or a group wherein R<SP>4</SP> is a C 1 or C 2 alkyl group, and R<SP>5</SP> is a C 1 -C 4 alkyl group; provided that when R<SP>3</SP> is a group, Z is other than alkoxy, R<SP>1</SP> is alkyl, and the alkyl groups represented by R<SP>1</SP> and R<SP>2</SP> each have a maximum of 4 carbon atoms; and further provided that when R<SP>3</SP> is a substituted or unsubstituted 1-cycloalken-1-yl group, the sum of the carbon atoms in R<SP>1</SP> and R<SP>2</SP> must be at least 4, is produced as follows:- (a) when Z = Cl, equimolar amounts of an imine of formula or R<SP>2</SP>N=R<SP>6</SP> where R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> are as defined above and R<SP>6</SP> is a cycloalkylidene group, and cyanuric chloride are reacted in an inert organic solvent at a temperature of from -25 to 30‹C. to form a 2,6-dichloro-4-[N-alkyl-N- (1-alken- or cycloalken-1-yl)-amino]-s-triazine of formula and the latter is reacted with an alkylamine of formula R<SP>1</SP>NH 2 at a temperature of from 10 to 45‹ C. to give the s-triazine of Formula I, (b) when Z = alkoxy or alkylthio an s-triazine as produced in (a) is reacted with an alkali metal alkoxide or an alkali metal salt of an alkyl mercaptan where the alkoxide or the alkyl mercaptan has from 1 to 4 carbon atoms, in the presence of an inert organic solvent. The compounds of the invention are used in herbicidal compositions.

Description

This invention relates to chemical agents for controlling undesirable vegetation in crops of cultivated crops. A herbicidal agent is known, which includes as an active substance methylthio-sim-triazine derivatives of the general formula S-CH 10 n n, a .- {f-kJt-i-Ki where R, R n or R N. 15 Rj C-jiHs. With Ndili N. However, the well-known herbicidal agent does not act selectively enough in crops of cereals. In order to enhance the herbicidal activity and selectivity of action, a herbicidal agent is proposed, including as an active substance methylthio-simm-triazine derivatives of the general formula H Rj iii-ir-4 -K-ii3 20 25 30 where Z is chlorine, carbon atoms R is alkyl or alkoxyalkyl with 1-B carbon atoms; alkyl with 1-8 carbon number; 1-cycloalken-1-yl with 5-7 carbon atoms or 1-cycloalken-3 substituted by lower alkyl or lower alkoxy residue: -yl or CH-C group is alkyl with carbon-i atoms where R is of genus 1-2; R t is alkyl with 1-4 carbon atoms, and if R 3 does not mean 1-cycloalken-1-yl, and Z is an alkoxy group, then R. is al.sil with no more than four carbon atoms, as well as each of alkyl residues denoted by R "denotes radicals R and Rij and if alkyl-1-cycloalken-1-yl, the sum of carbon atoms for alkyl residues denoted by radicals R and R can be at least four, and the content of active substance is 0.5- 95 wt.%.

In tab. given the physico-chemical characterization of the methylthiois-triaine derivatives of the indicated formula proposed as a herbicide.

Example. Weed seeds are sown in the soil,

Connection Name

4,6-Dichloro-2-pj-methyl-N - (1-cyclohexen-1-yl) amino-sym-triazine

2-Chloro-4-fN- (1-cyclohexen-1-yl) I -N-ethyl amino-b- (isopropylamino) -. β-triazine

2-Chloro-4- (ethylamino) -b-IN-ETHYL II -N- (1-cyclohexen-1-yl) amino-sim-triazine

2 Chloro-4- (3-methoxy-propylamino) IV-6-IN- (1-cyclohexen-1-yl) -N-methyl amino-simm-triazine

2-Chloro-4- (tert-butylamino) -6-N- (1-cyclohexen-1-yl) -M-ethyl amino-sim-triazine

2-Isopropylamino-4- -methyl-M- (1-cyclohexen-1-yl) amino-6-methoxy-Sym-triazium

2- (tert-Butylamine 6) -4 m- (1-cyclo I hexene-1-yl) -M-ethyl | amino-6-methoxy-simm-triazine

(1-Cyclohexen-1-yl) -M-meIII thyl-amino-4-methoxy-6- (3-methoxypropylamino) -s with 1mm-triazine

2- (Ethylamino) -4- N- (1-cyclgexen-1-yl) -N-ethylamino-b-methoxy-simmtriazine

2- (1-Cyclohexen-1-yl) -N-ethyl amino-4- {isopropylamino) -b-methoxy-sim-triazine-,

2-Isopropylamino-4-1y-methyl-M-.

I - (1-cyclohexen-1-yl) amino-6- (methylthio) -symm-triazine

2-N-Methyl-N- (1-cyclohexen-1-yl)

II amino-4- (3-methoxypropylamino) -6- (methylthio) -symm-triazine

2- (Ethylamino) -4- N- (1-cyclohexen-1-yl) -N-ethylZamino-b- (methylthio) -symn-triazine

2 N-Ethyl-N- (1-cyclohexen-1-yl)

IV amino-4- (isopropylamino) -b-methylthio-s-triazine.

After two weeks, the herbicidal activity was recorded according to the following scale: O - 0-25% of plants died; 1 - 50% of rasines died; 2 - dead as baud, dorishnik, impome, pepper, syt, wheatgrass, gumai, bonfire, hedgehog and at a dose of 1.12 kg / ha are treated with compounds 1-X IV indicated in. tab. one,

That l and c

Melting point, C

86-106

90-125

100-138

75-113

85-105

119-123

Rubbery substance

55-72

103-105 83-85 30-83 27-85 84-116

lo 75% of plants; 3 - full of death of plants.

The test results are presented in table 2.

Table

3 О О 1

2

3 1

Oh

3 3

Indian About

one

urn 2

32

3

31

oy3

0O

ABOUT

13

ABOUT

03

one

1o

1 1

one

PRI mme R 2. Comparative tests for the study of phytotoxicity for cultivated plants and herbicidal activity for weeds were carried out by treatment in which seeds of cultivated plants such as co, sugar beet, wheat, and rice, sorghum, and weed were sown. for example, hemp, fescue, Durishnik, buckwheat, impomei, pepper, millet,; firefire,; овsowberry, Elevein, Limnoharis, &amp; a dose of 1.12 kg / ha following compounds:

2-ethyl shno-4- |, M-ethyl-M- (2-methyl-1-propen-1-yl) amivo-b-methylthio-S-triazine (A), -.

2-methylamino-4-1 1-ethyl-M- (2-methyl-1-propen-1-yl) amino-b-methylthio-5-triazine (B),

2-isopropylamino-4-} 1-methyl- - (2-methyl-1-propen-1-yl) amino-b-methylthio-5-tRiazine (B1,

1 2 3 1 3

1 about o

about about about 1

1 o

3 1 o

1 о о 1

oh oh

13

LTD

about

about 1

about

3 2 3 2

oh oh

oh oh

2 about 3 3

2 3 2 3 О 1 О 2 3

oh oh

3 2 2 1 2 О 2 1

about

3 2

2 1

3 2 O 1 1 1 1

3

oh oh

oh oh oh

1 o o o

ABOUT

one

ABOUT

ABOUT

oh oh

1 about o

about about 1 about

one

about about about 1

1 about o

about about 1

about 1

2

3

2-isopropylamino-4-.N-ethyl-N- (2-methyl-1-propen-1-yl) amino-6-methylthio-5-triazine (g),

2-chloro-4-ethylamino-6-C-ethyl-H- (2-methyl-1-propen-1-yl) amine —S-triazine (D),

2-chloro-4-s-isopropyl-H- (2-methyl-1-propen-1-yl) amino-6-methylamino-S-triazine (E),

2-chloro-4- {isopropylamino) -6-m-ethyl-M- {2-methyl-1-propen-1-yl), c1mino | - $ - triazine (g),

2-tert-butylamino-4-M-methyl-M- (2-methyl-1-propen-1-yl) amino-6.-Methylthio-5-triazine (3).

After 2 weeks, an account was taken of the herbicidal activity and selectivity of action in points. The test results are presented in Table. 3

Table 3

000012121

20300

12322

3 3.2 3

   2

0001

About 01 About

3 .2 3 1

3132

2212 Example 3. Weed shoots of weeds at the age of 2 or 3 weeks, such as burdock, cocklebur, syt, ipome, fescue, pepper, limnoharis, wheatgrass, humay, bonfire and redberry, were treated at a dose of 4.5 kg / ha of compound 420343 Canadian loins 4 Durnishnik3041333 LimnoharisO 01 About 14 About Ipome 3042343 Tipchak.43-344. Water pepper 41-2. 430 CfeiTb0000110 Pyrey2023110 Gumay ..- About 00 20.1 koster 1111311 Ezhovnik2120323

Continued table. 3

Ltd

About 3

About 2 3 2 2

eleven

3 2

3 3

3

eleven

oh oh

12

3 3 3

12

eleven

1 DA 1-X IV, listed in Table. 1. Down. For 2 weeks, we recorded the herbicide of activity. According to the following scale: O - no damage, 4 - full of death. The test results are presented in Table. 4. Table4 -2. -4331 4343443 4 .13 2343 4232 333 42 44333 4 --- 3-3 6000111 10211.О1 - 1 2 О.-11 3013232 3 132222

Example 4: Plant seedlings, such as soybeans, sugar beets, wheat, rice, sorghum, as well as weeds, such as limnochemis, chicken millet, hemp pepper, buckwheat, buckwheat, elefsina, fire cinnamon trees, cocklebur, in stages 2 and 3 weeks were treated at a dose of 0.05 kg / ha with the following compounds:

2-ethylamino-4-M-ethyl-M- (2-methyl-1-propen-1-yl) amino-b-methylthio-S-triazine (A),

2- (methylamino) -4- M-ethyl-M- (2-methyl-1-gypropen-1-yl) amino-b-methylthio-5-triazine (B),

2-isopropylamino-4-LN-methyl-N- (2-methyl-1-propen-1-yl) amino-6-methylthio-5-triazine (c),

Example 5: Compounds: 2-ethylamino-4-N-ethyl-N- (2-methyl-1-propen-1-yl) amino-6-symm-triazine (A),

2- 1} -ethyl-H- (2-methyl-2-propan-l-yl) amino-4-ethylamino-6-methylthio-sim-triazine (c),

2-isopropylamino-4-m-ethyl-M- (2-methyl-1-propen-1-yl) amino-6-methylthio-5-triazine (g),

2-chloro-4-ethylamino-b- | N-ethyl-N- (2-methyl-1-propen-1-yl) amino-5-triazine (D) ,.

2-chloro-4-m-isopropyl-M- (2-methyl-1-propen-1-yl) amino | -6-methylamino-S-triazine (E),

2-chloro-4-isopropylamino-6-M-ethyl-N- {2-methyl-1-propen-1-yl) amino-5 -triazine (G),

2-tert-butylamino-4- {} | -methyl-K- (2-methyl-1-propen-1-yl) amino-6-methylthio-5-triazine (3),

2-chloro-4-tert-butylamino-B5-1 M-methyl-N- (2-methyl-1-propen-1-yl) amino-5-triazine (s).

The test results are taken into account after 2 weeks and are presented in table.5.

Table

2-chloro-4-ethylamino-b-M-ethyl-M- (2-methyl-1-propen-1-yl) a-Mino-syn-triazine (l) and

2-m-ethyl-M- (2-methyl-2-propen-1-yl) amino-4-ethylamino-6-chloro-symm

triazine (m)

At doses of 1.12 and 0.05 kg / ha, the crops were treated both before the appearance of seedlings and after their appearance, when test plants, such as soybeans, beets, wheat, rice, sorghum, and weeds, such as the cocktail, buckwheat, hemp, fescue., water pepper, limnoharis, bonfire, chicken millet, ryhovnik, elefsina, naye

O 3 O O O

About 1 2 1 3

Oh

About 3 3 2

Claims (1)

Herbicidal agent, comprising methylthio-simm-triazine derivatives as an active substance, as well as an additive selected from the group of solvent, emulsifier, dispersant, as follows: with the aim of enhancing herbicidal activity and selectivity of action, it is a compound of the general formula as methi-thio-sym-triazine derivatives. Z | KZ, where Z is chlorine, alkoxy or alkyl tibroup with 1-4 carbon atoms; walked in stage 2-3 leaves. Two weeks after the treatment of the crops, a gerbid activity was recorded on a 5-bg scale: 0 no damage, 1 and 2 weak damage, 3 moderate damage and 4 severe damage, 5 complete plant death. The test results are presented in Table 6. Table 6 one 1 о о о 1 O 2 O O O 3 4 1 1 Oh oh 1 2 O 2 O four ABOUT Ltd oh oh 3 ABOUT .1 2 1 3 2 3 O 1 1 3 4 3 3 oh oh oh oh oh 1 o Ltd 3 2 4 2 3 3 3 2 3 3 2 3 3 1 about 1 1 1 2 2 O O 2 1 about o 3 3 3 3 2 2. - alkyl or alkoxyalkyl with 1-8 carbon atoms; A is an alkyl with a carbon number of 1-8; 1-cycloalken-1-yl with 5-7 carbon atoms or substituted by lower alkyl or lower alkoxy residue - -cycloalken-1-yl, yl group 4 -sn-cg R. - alKyl with 1-2 carbon atoms; alkyl with 1-4 carbon atoms, if RjHe means 1-cyclone-1-yl, and Z is an alkoxy group, then alkyl with more than four carbon atoms, like each of the alkyl residues, is designated by the radicals f (and R, and , if Rj means alkyl 1-cycloalken-1-yl, then the sum of carbon atoms for alkyl residues designated by radicals Rj may be at least four, with the content of active substance being 0.5-95% by weight. Signs priorities: 04.01, 71 at X - chlorine or alkylthio group C, RJ-group-CH-C, RS alkyl, Rgr-alkyl with -Cd f, 24.03.71 with X - alkoxy, alkyl or alkoxy alkyl C -Cg, alkyl C -Cg, RJ-1-cycloalken-1-yl Cf-Cj or substituted by lower alkyl or lower alkyl-residue 1-cycloalken-G-yl or gr. U4 R4 alkyl, Rf-alkyl Q-C4 , provided that Rj does not mean 1-cycloalken-1-yl, Z is an alkoxy group, then R is an alkyl with a carbon number of not more than four, as well as each of the alkyl residues designated by the radicals R and RJ may have at least four.