CS197202B2 - Selective herbicide means - Google Patents

Description

The invention relates to a selective herbicidal composition for the selective control of monocotyledonous and dicotyledonous weeds in cereal crops, in particular in wheat, rye and barley crops.

U.S. Patent No. 2,655,455 discloses phenyl urea derivatives having herbicidal activity. Herbicidal activity results are also reported for some of these compounds. Thus, for example, 3- (p-chlorophenyl) -1,1-dimethylurea (Monuron), which controls monocotyledonous weeds, is described in Example 17. Example 18 of the same document first describes generally selective activity in cotton and then specifically states that 3 - (3,4-Dichlorophenyl) -1,1-dimethylurea (DIURON) and 3- (3-chloro-p-tolyl) -1,1-dimethylurea (Compound No. 17j destroys Halibut sorghum, a monocotyledonous plant).

On the basis of these data, it was not to be expected that one of the active substances which was demonstrably destroying monocotyledonous plants was to have a selective herbicidal activity in cultures of wheat, rye and barley, which are monocotyledonous plants.

The object of our invention is based on this surprising finding.

SUMMARY OF THE INVENTION The present invention provides a selective herbicidal composition for controlling monocotyledonous and dicotyledonous weeds in cereal crops, particularly in wheat, rye and barley crops, characterized in that it contains 1- (3-chloro-4-methyl) phenyl-3,3- dimethyl urea of formula I.

^Cl (I)

The composition of the invention has excellent crop selectivity against Apera, Aloperucus and Avena fatura.

With the compound of formula I, which forms the active ingredient of the composition according to the invention, monocotyledon weeds can be controlled in monocotyledon crops. In the case of weeds, both broadleaf weeds and grass weeds are suitable. For crops, grains, maize and similar monocotyledonous crops such as sugar beet, rice, and legume crops such as peanut and especially soybean crops are of particular interest. Both pre-emergence and post-emergence applications are contemplated. The amounts used can vary within wide limits, for example between 0.5 and 10 kg of active substance per ha; however, preferably 0.5 to 3.5 kg of active ingredient per ha are used.

and

The active ingredient according to the invention can be used alone or together with other herbicidally active substances or substances which influence growth. Examples of such substances include, but are not limited to:

CMPP, joxynil and its derivatives, bromoxynil and its derivatives, benzaldoximether, such as in particular 3,5-dibromo-4-hydroxybenzaldoxim-O-2,4-dinitrophenyl ether, urea derivatives such as neburon, fluomethurone, N- (3-chloro- 4-methoxyphenyl) -N ', N'-dimethylurea, N- (3-chloro-4-bromophenyl) N'-methyl-N'-methoxyurea, or triazine derivatives such as 2-ethylamino-4-tert-butylamino- 6-methylthio-s-triazine.

The active ingredient of the above-defined formula is known in the literature. It can be prepared in a manner known per se, for example by reacting an arylisocyanate of the formula II

Ct (II) with dimethylamine of formula III,

OII3 /

NH (III) \

CH 3 optionally in the presence of catalytic amounts of a tertiary amine such as triethylamine or triethylenediamine. 1- (3-chloro-4-methyl) phenyl-3,3-dimethylurea has a melting point of 147-148 ° C.

The compound of the invention can be used in a variety of ways. Thus, it can be formulated into emulsions, dusts and granules, etc. The conversion of the active ingredient into favorable dosage forms is generally known.

Example 1

A) Dust:

Equivalent parts of the active compound according to the invention and the precipitated silica are finely ground. By mixing with kaolin or talc, dusts can be prepared from this mixture preferably with 1 to 6% active ingredient.

B) Wettable powder:

To produce a wettable powder, for example, the following ingredients are mixed and finely ground:

20 parts by weight of the active compound according to the invention 20 parts by weight of highly adsorptive silica " Hisil "

3.5 parts of the reaction product of p-tert-octylphenol and ethylene oxide

1.5 parts by volume of 1-benzyl-2-stearylbenzimidazole-6,3‘-disulphonic acid sodium salt.

CJ Emulsifiable concentrate:

The emulsifiable concentrate is prepared according to the following formula:

parts of the active ingredient, parts of xylene, parts consisting of the reaction product of alkylphenol with ethylene oxide and calcium dodecylbenzenesulfonate are mixed. Dilution with water to the desired concentration produces a sprayable emulsion.

Example 2

and)

1- (3-Chloro-4-methyl) phenyl-3,3-dimethylurea shows a good action against various weeds in post-emergence application, saving corn, especially wheat.

Treatment was carried out with 2 and 1 kg / h and 12 days after sowing, when the plants reached the stage of 1-2 right leaves.

The following results have been achieved:

= no damage <5 = damage manifested> 5 = considerable damage 10 = plants totally dead plant used amount 1 and 2 kg / ha 1 2

Triticum Hordeum Avena sativa Sorghum Panicum Poa Triv. Dactylis Beta vulg. Calendula Linum us. Brass. rap. Daucus C. Lactuca Medicago Soya max Phaseolus

1 1 4 6 6 10 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 7 9 9 9

(b)

The active compound according to the invention, when applied pre-emergence, has a good effect against various weed species in the conservation of useful plants.

Treatment was carried out with 1 and 2 kg / ha one day after sowing.

The following results were achieved:

plant

Legend:

= no effect = still acceptable initial crop damage 6 = strong weed control 9 = total damage applied amount 1 and 2 kg / ha 1 2 soybean wheat

Sorghum rice

Avena fatua Digitaria Panic Poa

Alopecurus

Galium

Calendula

Ohrysanthemum

Brassica

Ipomoea

Stellaría

Amaranthus

Example 3

Comparative experiment

A field of various winter grain sown in autumn 1967, which was weed weed (Alopecurus), Apera species and numerous broadleaf weeds, was treated with different concentrations of the active compound of the invention (I) and the active compound of formula IV during March to April.

Cl

NH-CO-ν '\

(IV)

CN ^

The effective application rate of the compound of the invention (I) has always been well below that of the conventional active compound of the formula

IV. Effect values and number of grassy weeds are shown in the following table:

Experiment Compound Active substance Apera Number Matricaria Stellaria Alopecurus Number Status (number) kg / ha

Apera Alopecurus

Η H (COO) <N <M CT>

<N CO Tji rH CO

CO CM CO

ΙΏ O O-f CO * ^ f

Θ θ 'r-f CO w o> • i — i n · - <

tí

CD> ω 'tí tí' (Λ

It knows i t - t i rf t t ω

bo

CD hJ «I— (

P> O P-4 í <D ° t .. .. .. .. H H H

P-th three ω eat> th £ 44 th

CD

N

O> w 44 O <D and the third

O

Q o

thi thi thi

4- »three • three> N

CD>

ω

Γ — 1 cu o

P-i

4— · th

O

4tí

The active compound I according to the invention has been shown to produce better results, in particular in combating Apera and Alopecurus, at a significantly lower application rate than the comparative compound of formula IV.

The crop plant, ie wheat, was not adversely affected by this spring treatment.

The decisive factor for success is the right choice of the application rate, which lies far below the reference compound.

In a special experiment against Apera, it has been shown that even less application rates are sufficient to control this weed,

1.0

Alopecurus 3

Stellaria 2

Sinapis 2

Myosotls 3

Papaver 2 rye 1 (cultural plant)

Example 4

and)

The field, which was naturally weeded by Alopecurus, Stellaria, Sinapis, Myosotis and Papaver, was sown by rye. The active compound according to the invention (I) was applied by spraying onto the field immediately after sowing at a rate of 1.0, 2.0 and 3.0 kg / ha.

The result after 6 weeks is shown in the following table:

kg of active substance / ha I IV

2.0 3.0 3.0

17

114 2 16

2 7

116 13 1 = 100% weed control; full tolerance to crops = 98% weed control; very low lightening in culture at the beginning = 95% weed control; low light = no effect, resp. the total destruction of the cultural plant

(b)

A field infested naturally with whitegrass (Alopecurus) and various broadleaf weeds was sown with grain and immediately afterwards treated with the compound of the invention

1.0

Alopecurus 2

Stellaria 3

Sinapis 3

Myosotis 3 barley 1 = 100% weed control; full tolerance to crops = 98% weed control; very low lightening in culture at the beginning = 95% weed control; low light = no effect, resp. the total destruction of the cultural plant

2 3 9

C)

The field weed naturally (Alopecurus) was sown with wheat and (I) at 1.0, 2.0 and 3.0 kg of active ingredient per hectare.

Seven weeks after treatment, the following results were found:

kg of active substance / ha

I rv

2.0 3.0 3.0

8

4.2 3

2 1

2 2

1, 1.0, 2.0 and 3.0 kg of active ingredient were then treated immediately.

Four weeks later, the following results were found:

weed 1.0 kg of active substance / ha AND 2,0 3.0 IV 3.0 Alopecurus 2 2 2 9 Stellaria 3 2 2 6 Sinapis 2 2 1 5 wheat 1 1 2 1

= rear effect, resp. total destruction

Example 5

Comparative experiment:

Active substance of formula Q:

= 100% weed control; full tolerance to crops = 98% weed control; very low lightening in culture at the beginning = 95% weed control; poor lightening of the crop plant showed a good effect on various weeds in both preemergence and postemergence application, while wheat and barley were largely spared.

The treatment was performed once immediately after sowing and once 12 days after sowing (2 leaf stage) using 1 and 2 kg of active substance / ha.

The following results were achieved:

^Cy 5 ' ₌ y-W-CO-V-CU 1 a

Plant

Triticum

Hordeum

Avena sat.

Avena fat.

Alopecurus

Poa

Galium

Stellaria

Calendula

Legend:

= no effect 9 = total damage preemergence 2 kg / ha 1 kg / ha

3 1 4,5 1.5 8.5 7 8.5 7.5 9 6 9 6.5 4 1 9 9 8 1.5

post-emergence 2 kg / ha 1 kg / ha

2.5 1.5 4 2 7.5 5.5 8 8 9 5.5 9 5 7 4,5 9 9 9 4

Example 6

The effect of the compound of the formula I according to the invention was compared in the following test with the effect of the compounds of the formulas II and III known from the literature.

Compound of Formula I:

Compound of Formula II:

(known from U.S. Pat. No. 3,297,425)

Compound of formula III:

Cl OCHj [HU (known from US Patent No. 1 = no effect as control 3,288,586) 9 = plants completely dead

In the following tables, the numbers indicated have the following meanings: Comparison of the compounds of formula I and II:

(preemergence experiment) plants used rate 1 kg / ha compound I compound II wheat (Triticum) 2 barley (Hordeumj 1 maize (Zeaj 1 dew (Digitaria) 9 millet (Panicum) 8 foxtail (Alopecurus) 8 beet (Beta) 9 marigold ( Celandula) 8 Ipomoea 9 Stellaria 9 Amaranthus 9

The compound of formula I is selective in wheat.

barley and corn. The compound of formula II does not show any selectivity for the pre-emergence experiment.

Plants used amount 1 kg / ha Compound I Compound III Wheat (Triticum) 2 Rosette (Digitaria) 9 Millet (Panicum) 8 Foxtail (Alopecurus) 8 Marigold (Galendula) 8 Ramswort (Ipomoea) 9

9 3

Compound I is selective in wheat, while Compound III does not show selectivity.

Example 7

The following species of plants were sown in the greenhouse:

wheat (Triticum vulgare), barley (Hordeumj, oat (Avena sativa), millet (Panicům), meadowgrass (Poaj, foxtail (Alopecurus)).

The post-emergence treatment of said plant species was carried out with a 1% aqueous solution of a compound of formula I (according to the invention) and a compound of formula B cw ₃ o

Cl

NH-CO-IV (B) ch ₃ (known from French Patent No. 1 351 900), about 10 to 12 days after sowing, at a 2-3 leaf stage using 1 kg of active substance / ha. The evaluation was performed about 20 days after treatment, with the results shown in the following table:

CH,

NH-CO-N

Cl // (I) _X CH,

CH,

Comparison of the effect of compounds I and B on post-emergence application of 1 kg of active substance / ha.

plants: compounds

I B wheat (Triticum) barley (I-Iordeumj common oat (Avena sativa) millet (Panicum) meadow-grass (Poa) foxtail (Alopecurus)

Compound I is selective in wheat and barley, while Compound B does not show sufficient selectivity.

Michalka

1—2 no effect on plants

3–6 slight to moderate damage

7—9 severe to total damage

Example 8

Test for the possibility of selectively using known herbicidally active phenylurea derivatives in cereal crops by reducing their application rate

1. Perform the experiment

Seeds of weeds and / or crops are sown in pots filled with soil. The seeds are covered with a layer of soil about 1.5 cm high. Only on this soil surface are herbicides applied in the case of pre-emergence treatment 1 day after sowing, in an amount which after conversion in kg / ha is applied in 400 to 600 l of water / ha. By regularly watering these pots, the iherbicidal composition is dispersed in depth to the germinating seeds. The adsorption capacity of the formulations is, as in the field, dependent on physical properties.

For post-emergence application, the plants are treated at the 1-2 leaf stage 12 days after sowing. Herbicides are applied after the application rate in kg / ha has been recalculated in 400 to 600 l of water / ha. A portion of the application rate immediately reaches the spray rate in this spray as well as under practical conditions

3

4

6

6

5 top soil. This part gets regular watering to the roots of plants.

The active substances are used in amounts of 4 kg, 2 kg and 1 kg / ha in the form of wettable powders. The evaluation is performed after 20 days using a scale from 1 to 9 with the following meaning:

= no effect, perfect tolerability = complete destruction of crops and weeds up to 4 = reversible damage 5 to 8 = severe damage leading to gradual death

1./2. = 1st number means premergent application

2. number means post-emergence application

2. Sowed weed species and cultivar plants of foxtail (Alopecurus), meadow-grass (Poa), wheat and barley.

3. Active substances used

3.1

1- (4-chlorophenyl) -3,3-dimethylurea (MONURON)

3.2

1- (3,4-dichlorophenyl) -3,3-dimethylurea (DIURON)

3.3 l-phenyl-3,3-dimethylurea (FENURONj kg active Alopec - Poa wheat barley substance kg / ha rus

4. Results

MONURON 4 ‘9/9 9/9 9/9 9/9 2 9/9 9/9 9/9 9/8 1 8/9 8/9 9/9 7/7 DIURON 4 9/9 9/9 9/9 9/9 2 9/9 9/9 9/9 9/9 1 7/8 9/9 6/9 8/6 FENURON 4 8/8 9/9 9/9 9/9 2 8/8 9/9 6/7 6/8 1 6/7 8/7 3/7 4/5

5. Conclusion

By reducing the application rate of the herbicidally active phenylurea derivatives, i.e. Monuron, Diuron and Fenuron, which are structurally closest to the 1- (3-chloro-4-methyl) phenyl-3,3-dimethylurea used herein as a selective herbicide in crops There is no possibility of their selective application in the grain, and no effective application rates can be found which at the same time tolerate wheat and barley.

Example 9

Testing the biological properties of a compound of the invention, i.e. 1- (3-chloro-4-methyl) phenyl-3,3-dimethylurea and its isomer, i.e. 1- (4-chloro-3-methyl) phenyl-3,3 -dimethylurea at a rate of 4 kg / ha

The experiment, sown with weed species and crop plants, is otherwise the same as in Example 8.

1. Results of an experiment of kg of active Alopec-Poa substance / barley wheat

9/9

1- (3-Chloro-4-methylphenyl-3,3-dimethylurea 4)

1- (4-chloro-3-methyl) phenyl-3,3-dimethylurea 4 9/9

2. Conclusion

As expected, the test compounds exhibit the same herbicidal effect at the application rate corresponding to 4 kg / ha as the closely related known total herbicides MONURON, DIURON and FENURON (see Example 8).

Example 10

Testing of the biological properties of the compound proposed according to the invention, i.e. 1- (3-chloro).

kg active Aloplates / ha curus 1- (3-chloro-4-methyl) phenyl-4

-3,3-dimethylurea 21- (4-chloro-3-methyl) phenyl-4

-3,3-dimethylurea 2

9/9 9/9 ^9/9 9/9 9/9 9/9 9/9 9/9 9/9 9/8 9/9 9/7

9/9 8/8 8/8

9/9 9/9 9/9

-4-methyl) phenyl-3,3-dimethylurea, and its isomer, ie 1- (4-chloro-3-methyl) phenyl-3,3-dimethylurea, in parallel dilution series

The experiment, sown with weed species and crop plants, is analogous to Example 8. Numerical values

1/2.

The boxes in the boxes indicate the extent of good effect and compatibility.

Poa wheat barley

8/8 8/8 p7lZ_ 7/7 3/4 4/4 9/9 9/9 9/7 9/7 9/6 9/5

2. Conclusion

Contrary to expectations according to the results of the experiments given in Examples 8 and 9 above, it is surprising that the phytotoxic effect of the compound of the invention on wheat and barley - unlike its isomer - decreases in concentration to such an extent that unchanged weed activity there is a selectivity towards these types of grain.

Example 11

Further testing of the compound proposed according to the invention, i.e. 1- (3-chloro-4-methyl) phenyl-3,3-dimethylurea under conditions close to the field trial, i.e. under natural conditions, compared to 1- (3-chloro-4). (methoxy) phenyls with 1-3,3-dimethylurea known from the prior art (see French patent 1,497,868).

1. Legend

The application rate of 1- (3-chloro-4-methoxy) phenyl-1,3,3-dimethyl urea was 3.2 kg and 4.4 kg of active substance / ha, depending on the type of soil, depending on the soil type.

Pre = pre-emergence treatment

Post = post-emergence treatment% data - weed:% control against (untreated) control - crop culture:% yield against control (ie untreated control)

Scale:

= 100% action against weeds, no action against crop plant = no action against weeds, 100% action against crop plant

Numbers above 4 indicate insufficient weed control activity for the practical use.

2. Active substances used

2.1. 1- (3-chloro-4-methyl) phenyl-3,3-dimethylurea according to the invention (I)

2.2. 1- (3-chloro-4-methoxyphenyl-3,3-dimethylurea) according to French Patent Specification 1,497,868 (II)

Application of compounds I and II in the form of a wettable powder

3. Results

3.1 Field naturally infested with foxtail (Alopecurusj and oat (Avena j culture plant: winter wheat species: Joss Cambier country: Great Britain soil: clayey soil stage: 4th leaf - start of rooting)

effective substance kg of active substance / ha Alopecurus% extermination Avena fatua% extermination yield% I Post 2,0 73 68 124 2.4 85 78 135 3.2 97 95 152 II Post 4.4 87 89 131 Control 0 0 100 ALIGN! Comment 3.2 Natural way infested field To achieve approximately comparable result- cultural plant: winter wheat The amount of weed used in combating weeds Type: Splendeur Substance I o half less than the amount place: Chanceau / France winding substances II. With lower application rates soil: sand clay stvími se achieves a better increase yield. effective kg effective Alopecurus / Poa Yield% substance substances / ha index I Pre 2,0 3 126 3.0 2 115 II Pre 4.0 5 96 I Post 2.5 2 120 II Post 4.0 2 114

100 control

Comment:

Strongly improved weed control and yield increase by using compound I in smaller application rates. The amount of comparative substance II applied in this experiment corresponds to the official recommendations.

3.3 Field infested naturally with foxtail (Alopecurus) cultural plant: winter wheat species: Capelle place: Bourdigny / Switzerland soil: sandy clay ucinna substance kg active substance / ha

Alopecurus herds. F

Yield

I Post

II Post Control

2.4

4.0

196

156

100 ALIGN!

Comment:

In this extreme large weed trial, Compound I exhibits a significant improvement in weed control and yield yields at about half the amount of Comparative Compound II.

3.4 Field infested with foxtail (Alopecurus) culture plant: winter wheat species: Champlein place: Essertines / Switzerland soil: clay clay

effective substance kg of active substance / ha Alopecurus% Yield% I Post 2,0 88 213 2.4 96 222 3.0 99 229 II Post 4.0 49 156 control 0 100 ALIGN! Comment: 3.5 Field infested in a natural way foxtail (Alopecurus) The results show a significant prevalence of kv I against comparative substance II, both with- cultural plant : winter barley looking at applied quantity, also with regard to Type: Trust weed control e and increase the yield. place: Heilbronn / Germany soil: clay effective kg effective Alopecurus Yield% substance substances / ha index I Post 1.6 3 123 3.2 2 123 II Post 3.2 3 123 control 9 100 ALIGN! Comment: 3.6 Field infested naturally caused. but deaf Avena fatua Make using fabric ’I achieved the same

A weed-killing effect and increased yield, as in Comparative Substance II, is sufficient to use only 50% of its applied amount.

culture: winter wheat stage: end of rooting species: Moisson place: Vienne / France soil: lime clay effective substance kg active substance / ha

Avena fatua index wheat index

I Post

II Post Control

3.0

3.6

4.0

1.5

2.5 9

2.5

3.0

1.0

Comment

Compound (I) according to the invention shows a better action against deaf oats (Avena fatua) at a significantly lower application rate and at the same time is better tolerated by wheat culture than Comparative Compound II.

3.7 Field infested naturally with Avena fatua and Alopecurus culture: winter wheat stage: end of rooting (crops and weeds) species: Capitol place: Vienne / France soil: lime-clay

effective substance kg effective substances / ha Avena fatua index Alopecurus index wheat index I Post 3.0 2 1 2 4,5 1 1 2 II Post 4.0 6 2 1 6.0 5 1 2 control. 9 9 1

Comments: culture: winter barley stage: the end of rooting

With less active compound / ha, the compound I according to the invention is more effective than the comparator II. This also applies to considerably increased dosages of comparative substance II. 3.8 Field infested naturally with foxtail (Alopecurus) and ryegrass (Lolium) species: Noelle location: Neuilly le Sierra soil: stony clay soil effective substance kg of active substance / ha Alopecurus index Lolium Index barley yield in% I Post 2.4 1 1 94 3.6 1 1 92 II Post 4.0 2.5 2.5 86 control 9 9 100 ALIGN!

Comment:

Compound (I) of the present invention provides, with approximate fat content, at the same time, a better culture-better effect compared to Comparative (II).

3.7 Fields infested with natural weeds Avena sterilis culture: winter wheat stage: rooting center species: Mara country: Italy soil: clay

effective kg effective substance substances / ha I Post 2.4 3.2 II Post control Comment: 4.0

Avena sterilis wheat index index

1

1

1

1

A surprisingly good effect is achieved with half of the amount of the compound I applied according to the invention compared to the comparative substance II. Comparative substance II is virtually ineffective.

3.10 Fields infested with rye (Lolium) culture: winter wheat stage: beginning of rooting species: Estrella country: Spain soil: clay clay

effective substance kg of active substance / ha Lolium rigidum winter wheat index yield% I Post 2,0 2 135 II Post 4.0 6 131 control 9 100 ALIGN! Comment: cultural plant: winter barley stage: the beginning of rooting Surprisingly, the compound I according to the invention has a species: Aurora at 2.0 kg / ha, while comparative Country: Spain even at 4 kg of active substance / ha soil: clay clay bravely effective. 3.11 Field infested in a natural way ryegrass (Loliumj effective kg effective Lolium rigidum cultural plant substance substances / ha index index I Post 2,0 2 1 2.4 2 1 II Post 4.0 5 1 control 9 1

Comment:

The effect of Compound I is surprisingly good at 2.0 kg of active substance / ha and Compound II is insufficiently active at 4 kg of active substance / ha.

3. 12 Summary Comment

From the field results in monocotyledonous crops of useful plants which have been achieved under the conditions arriving in practice considered, results significantly better effect of 1- (3-chloro-4-methyl) ^{phenyl-3,3-dimethylurea:} urea (I) of compared to the effect of 1- (3-chloro-4-methoxy) phenyl-3,3-dimethylurea (II), which is known in the art, both in controlling weed grass and in terms of higher yield increases. in such cultures, at substantially lower rates of application of Compound I than Compound II.

Conclusion:

The results of the present series of tests confirm the nature of the invention and the technical progress of the compound proposed according to the invention, i.e. 1- (3-chloro-4-methyl) phenyl-1,3,3-dimethylurea, to selectively control monocotyledonous weeds in cereal crops.

Claims (1)

SUBJECT VYNALEZU A selective herbicidal composition for controlling monocotyledonous and dicotyledonous weeds in cereal crops, in particular in wheat, rye and barley crops, characterized in that it contains 1- (3-chloro-4-methylphenyl) -3,3-dimethylurea of the formula AND. CM 3 \ _ Cl HH-CO-N. (AND) Severography, n. P., Plant 7, Most