CH657752A5 - SELECTIVE HERBICIDES ON A TRIAZINONE BASE. - Google Patents

Description

The present invention relates to selective herbicidal compositions which contain a known 1,2,4-triazin-5-one, namely 4-amino-6-tert-butyl-3-ethylthio-1,2,4-triazine -5 (4H) -on, in combination with certain other known herbicidal active ingredients.

40 It has already become known that certain 3,6-di-substituted 4-amino-1,2,4-triazin-5- (4H) -ones can be used as herbicides (cf., for example, US Pat. Nos. 3,671,523 and 3 905 801). However, these triazinones are not always satisfactory when used for selective weed control 45. In practice, most triazinones pose difficulties when used for selective weed control of dicotyledon weeds and grass weeds in cereals. From the group of the described triazinones, 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -50 one (A) has found its way into practice and is preferably used for selective purposes Weed control used in soybeans, potatoes, tomatoes, alfalfa and, with severe restrictions, in cereals. The use in cereals primarily refers to post-emergence treatment. Use in 55 cereals in the pre-emergence process is not possible for reasons of compatibility. For reasons of phytotoxicity to the grain, the use is also only recommended for certain types of grain and also only for a limited area.

60 Furthermore, it is already known that 4-amino-6-tert-butyl-3-ethylthio-l, 2,4-triazin-5 (4H) -one (B) has general herbicidal properties (cf. US Pat. No. 3 671 523). However, special properties of this compound, in particular selective uses for this triazinone derivative in 65 crops, have not been previously known.

It has now surprisingly been found that the known 4-amino-6-tert-butyl-3-ethylthio-1,2,4-triazin-5 (4H) -one of the formula

(ch3) 3Cv | jX ^ N-NH2 (B)

^ NT 3C2H5

for the selective control, in particular of one and two-leaved weeds in cereal and legume crops, together with certain other known herbicidal active compounds before and after emergence of the plants, is very suitable.

Weeds in the broadest sense are understood to mean all plants that are usually used as impurities in cereals or Legume crops occur. Examples of weeds which are destroyed by the agents according to the invention and which occur frequently in cereal or legume crops are:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Cheno-podium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Cardi , Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.

Monocotyledonous weeds of the genera: Echinochloa, Se-taria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Scittiriruspus, Eleocharis , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

It was found that new combinations of active ingredients consisting of 4-amino-6-tert-butyl-3-ethylthio-l, 2,4-triazin-5 (4H) -one (B) and certain other known herbicidal active ingredients have a particularly high herbicidal activity and are outstandingly suitable for widening the spectrum of action and expanding the scope of application of triazinone (B).

Thus, when pre-sowing or pre-emergence, an agent according to the invention consisting of the triazinone (B) on the one hand and at least one of the compounds mentioned below are used:

(a) S-2,3,3-trichlorallyl-diisopropylthiol carbamate (Trialla-te),

(b) S-2,3-dichloroallyl diisopropylthiol carbamate (dialates) or

(c) l-Amino-6-ethylthio-3- (2,2-dimethylpropyl) -l, 3,5-triazine-2,4 (lH, 3H) -dione (ametridione)

on the other hand, used with particular success.

In the post-emergence treatment, the agent according to the invention is used which consists of the triazinone (B) on the one hand and at least one of the compounds mentioned below:

(c) l-amino-6-ethylthio-3- (2,2-dimethylpropyl) -l, 3,5-triazine-2,4 (lH, 3H) -dione (ametridione),

(d) 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (A) (metribuzin),

(e) 1,2-dimethyl-3,5-diphenyl-pyrazolium methyl sulfate (di-fenzoquat),

(f) ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate (benzoylprop-ethyl),

(g) isopropyl-N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate (flamprop-isopropyl),

(h) methyl-N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate (flamprop-methyl),

(i) 2 [4- (2,4-dichlorophenoxy) phenoxy] propionic acid methyl ester (diclofopmethyl),

657 752

(k) Methyl 2-chloro-3- (4-chlorophenyl) propionate (chlorfen-

prop-methyl),

(1) 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), (m) 3,5-diiodo-4-hydroxy-benzonitrile (ioxynil), (n) 2,4-dichlorophenoxyacetic acid (2,4-D ), (o) 2- (2,4-dichlorophenoxy) propionic acid (2,4-DP), (p) 4-chloro-2-methylphenoxyacetic acid (MCPA), (q) 2- (2-methyl-4- chlorophenoxy) propionic acid (MCPP), (r) l- (2-benzothiazolyl) -l, 3-dimethylurea (methabenzthiazuron),

(s) 3- (4-isopropylphenyl) -l, l-dimethylurea (isoproturon),

(t) 3- (3-chloro-4-methylphenyl) -1, l-dimethylurea

(Chlorotoluron) or (u) 3-isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide

(Bentazon)

on the other hand.

The combination of active substances consisting of the triazinones (B) + (A) is particularly preferred for post-emergence treatment (ie in the post-emergence method).

The herbicidal activity of the active compound combinations mentioned is surprisingly greater than the sum of the effects of the individual components, i.e. the active ingredient combinations show a synergistic effect. The new active ingredient combinations thus also represent a valuable addition to the technology.

The weight ratios of the active substances in the active substance combinations can fluctuate in relatively large ranges. In general, from 1 part by weight of triazinone (B) 0.02 to 10 parts by weight of the mixture partners mentioned, preferably 0.05 to 4 parts by weight.

The active ingredient combinations according to the invention can be used in the same plants as the active ingredient (B) alone.

The new combinations of active substances mentioned can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymers Fabrics.

These formulations are usually prepared in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl formamide and dimethyl sulfoxide, and water. The following are suitable as solid carriers:

E.g. natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules

3rd

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

657 752

organic materials such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-generating agents come into question: z. B. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.

In the formulations, dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue, and organic dyes such as alizarin, azo and metal phthalocyanine dyes, and also trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, can be used as further additives and zinc can be used.

The formulations generally contain between

0.1 and 95 percent by weight of active ingredient combination, preferably between 0.5 and 90%.

The active compound combinations according to the invention are generally used in the form of finished formulations. The active substances contained in the active substance combinations can also be mixed as individual formulations during use, i.e. be used in the form of tank mixes.

The new active ingredient combinations, as such or in their formulations, can furthermore also be used in a mixture with other known cereal or legume herbicides, ready-to-use formulations or tank mixes being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.

The new active ingredient combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application can be done in a conventional manner, e.g. B. by pouring, spraying, spraying, dusting or scattering.

While triazinone (A) can only be used in cereals using the "post-emergence" process, and then only with the other restrictions mentioned, it is possible to use the aforementioned new active ingredient combinations in cereals both in "post-emergence" - as well as in the "pre-emergence" procedure. The new active ingredient combinations can also be worked into the soil before sowing.

The amount of active ingredient used can fluctuate in larger areas, it depends, among other things. depending on the weather and soil factors. In general, the application rates are between 0.01 and 5 kg of active ingredient combination per ha, preferably between 0.1 and 3 kg / ha.

The following examples serve to explain the invention further.

Manufacturing examples

1. 4-amino-6-tert-butyl-3-ethylthio-l, 2,4-triazin-5 (4H) -one (B)

To a solution of 1000 g (5 mol) of 4-amino-6-tert-butyl-3-mercapto-l, 2,4-triazin-5 (4H) -one (cf. US Pat. No. 3,671,523) in 5250 ml of sodium hydroxide solution are added to 5 ml of an alkyl aryl polyglycol ether as emulsifier and 572 g (5.25 mol) of ethyl bromide. Stir vigorously at 50 C until the pH

The aqueous phase has dropped to 7-8 (10-12 hours). After cooling to 20 ° C., the reaction product which has crystallized out is filtered off with suction, washed several times with water and dried at 50 ° C. 1050 g (92% of theory) of an isomer mixture melting at 77 ° -82 ° C. and having the following composition, determined by gas chromatography:

10th

81%

(ch3) 3c

V

YYNH2

SC2H!

20 19% (ch3) 3c v ^ N-N

1 ace

25th

N c2h5

4-amino-6-tert.-

butyl-3-ethyl

thio-l, 2,4-tri-

azin-5 (4H) -one

(B)

4-amino-6-tert-butyl-2-ethyl-1,2,4-triazin-5 (4H) -one-3- (2H) -thione (C)

The pure 3-ethylthio derivative (B) with a melting point of 30 95 ° C. can easily be separated off by redissolving the isomer mixture of cyclohexane.

If the equivalent amount of ethyl iodide is used instead of ethyl bromide, the two isomers (B) and (C) are formed in a ratio of 90:10.

35

2. Formulation example:

The procedure for producing a 60% wettable powder is as follows:

60 parts by weight of triazinone (B) from technical active ingredient 40 3 parts by weight of arylalkyl sulfonate

3 parts by weight of sulfite waste liquor (spray-dried) 5 parts by weight of formaldehyde-cyclohexanone-Na-bisulfite-

Condensate 10 parts by weight of highly disperse silica 4S remainder (per 100 parts by weight) of alumina are mixed in a Lödiger mixer and then ground using an 8-inch jet mill.

The formulation thus prepared can be suspended in water and is used to prepare a ready-to-use spray formulation.

Application examples In all examples:

(A) = 4-amino-6-tert-butyl-3-methylthio-l, 2,4-triazin-5 (4H) -one

55 (B) = 4-amino-6-tert-butyl-3-ethylthio-l, 2,4-triazin-5 (4H) -one

Explanation of abbreviations:

PANMI

=

[\ micuin miliaceum so SINAL

=

Sinapis alba

GASPA

=

Galinsoga parviflora

STEME

=

Stellaria media

CHEAL

=

Chenopodium album

LAMSS

=

Lamium spec.

it POLCO

=

Polygonum convolvulus

POLLA

=

Polygonum lapathifolium

VIOTR

=

Viola tricolor

RAPRA

Raphanus raphanistrum

GALAP = Galium aparine POLAV = Polygonum aviculare

Example A Post emergence test / greenhouse

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

5 657 752

Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the amounts of active compound shown in the table are applied per unit area. The concentration of the spray liquor 5 is chosen so that the amounts of active ingredient given in the table are applied in 20001 water / ha. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

OK 0% = no effect (like untreated control) 100% = total destruction

Active ingredients, application rates and results are shown in Table A below:

Table A

Post emergence test / greenhouse

Active ingredient - PANMI SINAL GASPA STEME Wheat Maize expenditure kg / ha

(A) 1.0 0.5 0.25

(B) 1.0 0.5 0.25

100 100

100 100

100 100

100 100

100 100

95 100

100

100

100

100

100

100

100

100

100

100

100

90

100

90

90

90

90

70

20th

80

0

20th

0

0

Example B Post emergence test / field In a multi-species experiment on sandy loam with a medium humus content, summer wheat, summer barley and peas were sown. The sowing took place on May 8th. The herbicide treatment was carried out after 33 days on June 10, that is, the post-emergence process. The weeds were in the 4-6 leaf stage at the time of treatment. The specified amounts of active ingredient were applied in 5001 water / ha. The active ingredients were triazinone (A) formulated as 70% wettable powder and triazinone (B) formulated as 60% wettable powder. The parcel size was 10 m2. The herbicidal activity was measured on the naturally occurring weed population. The effect on weeds and crops was recorded in percent damage in comparison to the untreated control and is summarized in Table B below:

Table B

Post emergence test / field

Active ingredient Active ingredient- CHEAL RAPRA GALAP POLCO POLAV Summer- summer pea expenditure kg / ha

barley wheat

2.0

100

100

90

100

100

95

70

70

1.5

100

100

85

100

100

90

50

50

1.0

100

100

80

100

100

85

30th

30th

0.5

100

100

75

100

100

30th

10th

10th

2.0

100

100

100

100

100

10th

0

15

1.5

100

100

95

100

100

5

0

10th

1.0

100

100

90

100

100

0

0

5

0.5

100

100

80

100

100

0

0

0

Example C Pre-emergence test / greenhouse In a greenhouse experiment, different types of grain were checked in seed trays for their reaction against herbicides. Seed trays (size 20 x 20 cm) were filled with sandy loam with a humus content of 2.2%.

After sowing the different types of grain, the spraying took place in a spray booth on the same day, i.e. in the pre-emergence process. The amount of active ingredient was applied in 4201 water / ha. The evaluation was carried out 4 weeks after sowing. The effect was rated as percentage damage in comparison to the untreated control and is summarized in Table C below:

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6

Table C.

Pre-emergence test / greenhouse

Active ingredient

Active ingredient expenditure kg / ha

Wheat Neepawa

triumph

Wascana

Barley Larker

Bonanza

Was

(A)

0.5

87

100

100

100

97

100

0.25

17th

60

63

25th

10th

17th

0.125

0

2nd

10th

3rd

2nd

8th

(B)

0.5

0

2nd

18th

3rd

8th

12

0.25

0

0

10th

0

0

10th

0.125

0

0

2nd

0

0

0

Example D Pre-emergence test / field In a multi-species experiment on sandy loam with a medium humus content, summer wheat, summer barley and peas were sown. The sowing took place on May 8th. The herbicide treatment occurred on the same day as the pre-emergence procedure. The specified amounts of active ingredient were applied in 5001 water / ha. The active ingredients were triazinone (A) formulated as 70% wettable powder and triazinone (B) formulated as 60% wettable powder. The parcel size was 10 m2. The herbicidal activity was measured on the naturally occurring weed population.

20 The effect on weeds and crops was recorded in percent damage in comparison to the untreated control and is summarized in Table D below:

Table D

Pre-emergence test / field

Active ingredient

Active ingredient

CHEAL

LAMSS

POLCO

summer

summer

Peas

expenditure kg / ha

barley wheat

(A)

2.0

100

100

100

50

30th

70

1.5

100

100

100

30th

10th

50

1.0

100

95

100

20th

5

30th

0.5

95

90

95

10th

0

10th

(B)

2.0

95

100

100

10th

10th

10th

1.5

90

100

100

0

0

0

1.0

85

95

95

0

0

0

0.5

75

80

90

0

0

0

Example E Pre-emergence test / field In a multi-species experiment on sandy loam with a medium humus content, summer wheat, summer barley and peas were sown. The sowing took place on May 20, the herbicide treatment was carried out on the following day, ie in the pre-emergence process. The specified amounts of active ingredient were applied in 5001 water / ha.

The active ingredients were triazinone (A) formulated as 70% wettable powder and triazinone (B) formulated as 60% 45 wettable powder. The plot size was 10 m2. The herbicidal activity was measured on the naturally occurring weed population. The effect on weeds and crops was recorded in percent damage compared to the untreated control and is summarized in Table E below:

Table E

Pre-emergence test / field

Active ingredient

Active ingredient expenditure kg / ha

POLLA

VIOTR

LAMSS

POLCO

Spring barley

Summer wheat

egg

(A)

2.0

100

100

100

100

50

50

5

1.5

98

100

100

95

20th

30th

0

1.0

95

98

95

90

10th

20th

0

0.5

85

95

90

85

5

10th

0

(B)

2.0

100

100

100

100

0

0

0

1.5

100

95

100

95

0

0

0

1.0

95

90

95

90

0

0

0

0.5

85

70

85

80

0

0

0

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Example F Pre-sowing incorporation / greenhouse In a greenhouse experiment, various types of grain were checked in seed trays for their reaction against herbicides. Seed trays (size 20 x 20 cm) were filled with sandy loam with a humus content of 2.2%. The spraying took place in a spray booth. The amounts of active ingredient were applied in 4201 water / ha. After

The active ingredient was sprayed into the soil and then the various cereals were sown. The application was therefore carried out in the pre-sowing process. The evaluation was carried out 4 weeks after sowing. The effect was rated as percentage damage compared to the untreated control and is summarized in Table F below:

Table F

Pre-seed incorporation / Greenhouse Active ingredient Active ingredient- Wheat expenditure kg / ha Neepawa

Triumph Wascana

Barley Larker

Bonanza

Was

(A) 0.5 0.25 0.125

(B) 0.5 0.25 0.125

100

100

25th

57

3rd

15

8th

15

3rd

5

0

0

100

100

90

75

27th

12

8th

3rd

0

0

0

0

100

100

63

17th

17th

8th

8th

12

0

10th

0

0

Example G

Individual field plots were planted with herbicides (A) and (B), 4-amino-6-tert-butyl-3-methylthio-l, 2,4-triazin-5 (4H) -one and its 3rd -Ethylthio homologs, treated by spreading them in various application rates (kg / ha) over the surface of the soil and then working them in with the rotating tiller to a depth of about 10 cm. On the same day, 30 wheat and barley were sown in rows in the plots.

abbreviation

Botanical name

Common name

AMARE

Amaranthus

Bow amaranth

retroflexus

(Foxtail)

AMBEL

ambrosia

Jacob's herb

artemisiifolia

AVEFA

Avena fatua

Airport oats (wind

oats)

BRAPI

Brachiaria piligera

-

CHEAL

Chenopodium album common goose foot

DATE

Datura stramonium common thorn apple

DIGSA

Digitaria sanguinalis

Blood millet, finger grass

ECHCG

Echinochloa crus-galli

Chicken millet

GAETE

Galeopsis tetrahit

Field down

HELAN

Helianthus annuus

Sunflower

POLPE

Polygonum persicaria

Flea knotweed

POLSC

Polygonum scabrum

Green knotweed

monk

SETVI

Setaria viridis

Bristle millet, Fennich

Four weeks later, the extent of damage was assessed visually by comparison with neighboring untreated control plots. The evaluation for each of the weed species was based on the combination of four plots that had been treated with the same herbicide concentration. The herbicide concentration that caused damage of at most 15% was determined for each crop type. For each weed species, the concentration was determined that caused at least 80 percent control.

Tables G and H show the results for the two herbicides and the individual weed species for the two crop types. The vertical straight lines ss denote the acceptable concentration for each crop type, and for a specified weed species, "X" to the right of this straight line means that the weeds are not successfully controlled by a concentration suitable for the crop type. If “X” is entered to the left of this Gera-60, this means that weeds have been successfully controlled.

The longer the horizontal distance to the left of the vertical straight line, the larger the safety area ^ when using the special herbicide.

65

The tables show that the 3-ethylthio homologue is superior to the 3-methylthio homologue in the crop species indicated.

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Table G wheat

Application rate of herbicide (B) for pre-emergence treatment

(kg / ha)

weed

Active ingredient (B) 0.25 0.375

0.5

0.75

1.0

1.25

1.5

2.0

3.0

4.5

AVEFA

AMARE

CHEAL

POLSC

(GAETE)

AVEFA

SETVI

CHEAL

AVEFA

X

SETVI AMARE

X

X

CHEAL

X

X

>

AVEFA

2 ^

BRAPI

(DIGSA)

(ECHOG)

AMARE

X

AMBEL

X

CHEAL

X

DATE

X

HELAN

X

X X

X

X

AVEFA

X

AMARE

X

CHEAL

X

POLSC

X

AVEFA

X

POLPE

X

AVEFA

X

SETVI

POLPE

X

>

Table G - continuation of wheat / comparative tests application rate of the herbicide (A) with pre-emergence treatment (kg / ha)

weed

Active ingredient (A) 0.1 0.15

0.2

0.25 0.375

0.5

0.75 1.0

1.25

1.5

AVEFA

SETVI

AMARE

CHEAL

AVEFA

AMARE

CHEAL

POLSC

(GAETE)

AVEFA

BRAPI

(DIGSA)

(ECHOG)

AMARE

AMBEL

CHEAL

DATE

HELAN

X

X

X X X

X

X X X

X_ X

X

X X X

9

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Weed active ingredient (A)

0.1 0.15 0.2 0.25 0.375 0.5 0.75 1.0 1.25 1.5

AVEFA

X

SETVI

X

CHEAL

X

AVEFA

X

AMARE

1

i r L

CHEAL

J

r

L

POLSC

2nd

r L

AVEFA 1

X

POLPE 1

X

AVEFA

X

SETVI

X

POLPE

X

Notes on Table G:

The vertical straight line denotes the application rate at which the damage to the crop type was within tolerable limits, i.e. were no more than 10 to 15%.

"X" denotes the application rate at which each individual weed species was combated to an economically reasonable extent, i.e. about 80%.

If the symbol "X" is on the vertical straight line, economic control is only achieved with the highest, still tolerable application rate. If the "X" sign is to the left of the vertical straight line, weed control is successful at a rate which is lower than the tolerance limit for the crop type. The horizontal connecting line between "X" and the vertical line indicates selective weed control, and the length of the line indicates the safety area.

30th

35

Table H barley

Application rate of herbicide (B) for pre-emergence treatment (kg / ha)

Weed active ingredient (B)

0.25 0.375 0.5 0.75 1.0

1.25 1.5 2.0 3.0

4.5

AVEFA

AMARE

CHEAL

POLSC

GAETE

(AVEFA)

(SETVI)

CHEAL

AVEFA

AMARE

CHEAL

POLSC

AVEFA

POLPE

AVEFA

(SETVI)

POLPE

X

X_ x_ X. X

X_

x_

X

X

X X

X

X

AVEFA

X

SETVI

X

AMARE

X

CHEAL

X

X

X

>

752 10

Table H - Continuation of barley / comparative tests Application rate of the herbicide (A) with pre-emergence treatment (kg, ha)

Weed active ingredient (B)

0.1 0.15 0.2 0.25 0.375 0.5 0.75 1.0 1.25 1.5

AVEFA

SETVI

AMARE

CHEAL

AVEFA X

AMARE

CHEAL

X

POLSC

X

GAETE

X

(AVEFA)

(SETVI)

CHEAL

X

AVEFA

AMARE

X

CHEAL

X

POLSC

X

AVEFA I

X

POLPE 1

X

AVEFA

(SETVI)

POLPE

X

X

X X

X

X X

X

X X X

Notes on Table H:

The vertical straight line denotes the application rate at which the damage to the crop was within tolerable limits, i.e. were no more than 10 to 15%.

“X” denotes the application rate at which each weed species was combated to an economically justifiable degree (approximately 80%).

If the symbol "X" is on the vertical straight line, economic control is only achieved with the highest, still tolerable application rate. If the "X" sign is to the left of the vertical straight line, weed control is successful at a rate which is lower than the tolerance limit for the crop type. The horizontal connecting line between "X" and the vertical line is then characteristic of selective weed control, and the length of the line indicates the safety area.

45

50

55

60

65

Claims (2)

657 752 2 PATENT CLAIMS 1. Selective herbicidal agent for use in the pre-emergence process and for pre-sowing incorporation, characterized by a content of an active ingredient combination consisting of (l) 4-amino-6-tert-butyl-3-ethylthio-1,2 , 4-triazin-5 (4H) -one of the formula (ch3) -3c U yVH2 NnN ^ SC2H ^ (b) and (2) at least one of the following compounds: (a) S-2,3,3-trichlorallyl -diisopropyl-thiol carbamate; (b) S-2,3-dichlorallyl-diisopropylthiolcarbamate or (c) 1-amino-6-ethylthio-3- (2,2-dimethylpropyl) -l, 3,5-triazine-2,4 (1H, 3H) -dione. 2. Herbicidal composition according to claim 1, characterized in that the weight ratio of component (1) to component (2) in the active ingredient combination is between 1: 0.02 and 1:10. 3. Herbicidal composition according to claim 2, characterized in that the weight ratio of component (1) to component (2) in the active ingredient combination is between 1: 0.05 and 1: 4. 4. A process for selective weed control in the pre-emergence process or in the pre-sowing incorporation into cereal and legume crops using the herbicidal composition according to one of claims 1 to 3. 5. Selective herbicidal composition for use in the post-emergence process, characterized by containing an active ingredient combination of (1) 4-amino-6-tert-butyl-3-ethylthio-l, 2,4-triazin-5 (4H) -one i5 and (2) 4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one. 7. Herbicidal composition according to claim 5 or 6, characterized in that in the active ingredient combination the 20 weight ratio of component (1) to component (2) is between 1: 0.02 and 1:10. 8. Herbicidal composition according to claim 7, characterized in that in the active ingredient combination the weight ratio of component (1) to component (2) 2s is between 1: 0.05 and 1: 4. 9. Process for selective weed control in the post-emergence process in cereal and legume crops using the herbicidal composition according to one of claims 5 to 8. <ch3) 3c o yVH2 NnH ^ SC2H5 (b) and (1) 3,5-dibromo-4-hydroxy-benzonitrile (m) 3,5-diiodo-4-hydroxy-benzonitrile, (n) 2,4-dichlorophenoxyacetic acid, (0) 2- (2,4-dichlorophenoxy) propionic acid, s (p) 4-chloro-2-methylphenoxyacetic acid, (q) 2- (2-methyl-4-chlorophenoxy) propionic acid, (r) 1 - (2-benzothiazolyl) -1,3-dimethylurea, (s) 3- (4-isopropylphenyl) -l, l-dimethylurea , (t) 3- (3-Chloro-4-methylphenyl) -l, l-dimethylurea or io (u) 3-isopropyl-2, l, 3-benzo-thiadiazinon- (4) -2,2-dioxide. 6. Herbicidal composition according to claim 5, characterized by a content of an active ingredient combination consisting of (1) 4-Amino-6-tert-butyl-3-ethylthio-l, 2,4-triazin-5 (4H) -one of the formula (2) at least one of the following compounds: (c) 1-amino-6-ethylthio-3- (2,2-dimethylpropyl) -1,3,5-triazine-2,4 (1H, 3H) -dione, (d) 4-amino-6-tert-butyl-3-methylthio-l, 2,4-triazin-5 (4H) -one (A), (e) 1,2-dimethyl-3,5-diphenyl-pyrazolium methyl sulfate, (f) ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate, (g) isopropyl-N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate, (h) methyl-N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate, (i) methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate, (k) methyl 2-chloro-3- (4-chlorophenyl) propionate,