DE1567032B2 - Herbicides - Google Patents

Description

It is known to weed with N-fluorophenyl-N'-methylurea to fight. The known 3-fluorophenyl derivative (US Pat. No. 2,655,447) has however, it does not always have sufficient activity.

In contrast, the weed control composition according to the invention is characterized by a 3- (o-Fluorophenyl) -l-methylurea content.

The active ingredient obtained according to the invention is significantly more water-soluble than known herbicides of the * Commercial and more active than the well-known m-fluoro derivative.

The active ingredient according to the invention is used in conventional preparation forms for herbicides used. Usually these contain the 3- (o-fluorophenyl) -l-methylurea and one or several surfactants.

The surface active agent for the purposes of the invention can be a wetting, dispersing or emulsifying agent which assists the dispersion of the compound. These surfactants include anionic, cationic and non-ionic agents that have been generally similar to date in plant regulators Type used.

In general, the surfactant is used in the weed control compositions according to the invention used in an amount of less than 10 percent by weight. Usually 1 to 5% work, but quantities below 1% can also be used.

To increase the weight ratio of the surfactant to the active ingredient to high values, like 5: 1, further surface-active agents can be added to the above preparation. The addition of bigger ones Amounts of surfactant are normally intended to increase the herbicidal effect of the active ingredient to reinforce. When using larger amounts, the surfactant is preferably in one Amount from Vs to 5 parts per part of 3- (o-fluorophenyl) -1-methylurea used.

The herbicides according to the invention can be used in addition to the surfactant also contain finely divided diluents such as talc, natural clay, including attapulgite and Kaolinite clay, pyrophyllite, kieselguhr, synthetic, fine silicon dioxides, calcium silicate, carbonates, calcium phosphates, Sulfur, lime and flours such as walnut shell, wheat, redwood, soybean and Cottonseed flour.

You can use the finely divided, inert solids diluent in very different amounts, but will generally work with 10 to 98% of the weight of the herbicide. Particle size can also vary widely, but usually one size will go with one work below 50 microns in the finished preparation.

The preparations containing 3- (o-fluorophenyl) -l-methylurea can be used in a preferred manner are in the form of wettable powders. In addition to the active ingredient, these contain one or more surfactants and one or more finely divided, inert solid diluents of the above described type. If desired, other ingredients can be added, such as corrosion inhibitors, Adhesives, anti-foaming agents, pigments and the like.

These wettable powders can be obtained by mixing the ingredients and then adding the preparation a hammer mill, air abrasion mill or similar device. Contain such wettable powders 10 to 90% of the active ingredient, 1 to 5% surface-active agent, the remainder a finely divided, inert diluent, optionally together with one or more other additives. The particle size of the preparation is preferably below 50 microns.

The active ingredient according to the invention can also be used in others which are customary for combating weeds Preparations are used, such as emulsifiable oil solutions, granules, pellets and aqueous suspension concentrates.

The 3- (o-fluorophenyl) -l-methylurea can also be mixed with other herbicides to form a mixture mix of extraordinarily broad herbicidal activity. The following connections are made to the Mix in the proportions given below.

Substituted ureas

3- (3,4-dichlorophenyl) -l, l-dimethylurea, 3- (4-chlorophenyl) -l, l-dimethylurea, 3-phenyl-1,1-dimethylurea, 3- (3,4-dichlorophenyl) -l-n-butyl-l-methyl-

urea,
3- (3,4-dichlorophenyl) -l-methoxy-l-methylurea,

3- (4-chlorophenyl) -1-methoxy-1-methylurea, 3- (3,4-dichlorophenyl) -l, l, 3-trimethylurea, 3- (p-chlorophenoxyphenyl) -l, 1-dimethylurea, '
1- (2-methylcyclohexyl) -3-phenylurea.

These ureas can be mixed with the 3 ~ (o-fluorophenyl) -1-methylurea used according to the invention be mixed in proportions of 1: 4 to 4: 1, a ratio of 1: 2 to 2: 1 is preferred.

Substituted triazines

2-chloro-4,6-bis- (ethylamino) -s-triazine, 2-chloro-4-ethylamino-6-isopropylaminos-triazine,

2-chloro-4,6-bis- (methoxypropylamino) -s-triazine, 2-methoxy-4,6-bis- (isopropylamino) -s-triazine, 2-methylmercapto-4,6-bis (isopropylamino) -

s-triazine,
2-methylmercapto-4,6-bis (ethylamino) -

s-triazine,
2-methylmercapto-4-ethylamino-6-isopropylamino-s-triazine,

2-methoxy-4,6-bis (ethylamino) -s-triazine, 2-methoxy-4-ethylamino-6-isopropylamino-

s-triazine,
2-chloro-4,6-bis (isopropylamino) -s-triazine.

These triazines can be mixed with 3- (o-fluoropheriyl) -l-methylurea be mixed in proportions of 1: 4 to 4: 1, a ratio of 1: 2 to 2: 1 being preferred will.

Phenols

Dinitro-o-sec-butylphenol and its salts, Pentachlorophenol and its salts.

These phenols can be mixed with 3- (o-fluorophenyl) -l-methylurea in proportions of 1:10 to 20: 1 with a ratio of 1: 5 to 5: 1 being preferred.

Carboxylic acids and their derivatives

With 3- (o-fluorophenyl) -l-methylurea, the following carboxylic acids and derivatives thereof can be used in mixed in the following proportions:

,

A. 2,3,6-Trichlorobenzoic acid and its salts,

2,3,5,6-tetrachlorobenzoic acid and its salts, 2-methoxy-3,5,6-trichlorobenzoic acid and its

Salts,
2-methoxy-3,6-dichlorobenzoic acid and its salts,

3-amino-2,5-dichlorobenzoic acid and its salts, 3-nitro-2,5-dichlorobenzoic acid and its salts, 2-methyl-3,6-dichlorobenzoic acid and its salts, 2,4-dichlorophenoxyacetic acid and its salts

and esters,
2,4,5-trichlorophenoxyacetic acid and its salts

and esters,
(2-methyl-4-chlorophenoxy) acetic acid and its salts and esters,

. 2- (2,4,5-trichlorophenoxy) propionic acid and

and their salts and esters,
2- (2,4,5-trichlorophenoxy) -ethyl-2,2-dichloro-

propionate,
4- (2,4-dichlorophenoxy) butyric acid and its

Salts and esters,
4- (2-methyl-4-chlorophenoxy) butyric acid and

their salts and esters,
2,3,6-trichlorobenzyloxypropanol. Mixture in a ratio of 1:16 to 8: 1, preferably 1: 4 to 4: 1.

B. 2,6-dichlorobenzonitrile.

Mixing in the ratio of 1: 4 to 4: 1, preferably 1: 3 to 3: 1.

C. Trichloroacetic acid and its salts. Mixing in the ratio of 1: 2 to 25: 1, preferably 1: 1 to 8: 1.

D. 2,2-dichloropropionic acid and its salts. Mixing in the ratio of 1: 4 to 8: 1, preferably 1: 2 to 4: 1.

E. N, N-di- (n-propyl) -thiolcarbamic acid, ethyl ester,
N, N-di- (n-propyl) -thiolcarbamic acid,

N-propyl ester,
N-ethyl-N- (n-butyl) -thiolcarbamic acid,

Ethyl ester,
N-ethyl-N- (n-butyl) -thiolcarbamic acid, n-propyl ester.

Mixture in the ratio of 1: 2 to 24: 1, preferably 1: 1 to 12: 1.

F. N-phenylcarbamic acid, 2-methylcyclohexyl-

ester,
N-phenylcarbamic acid, isopropyl ester, N- (m-chlorophenyl) -carbamic acid, isopropyl ester,: N- (m-chlorophenyl) -carbamic acid, 4-chloro-2-butynyl ester.

Mixture in the ratio of 1: 2 to 24: 1, preferably 1: 1 to 12: 1.

G. 2,3,6-Trichlorophenylacetic acid and its salts. Mixture in the ratio of 1:12 to 8: 1, preferably 1: 4 to 4: 1.

H. 2-chloro-N, N-diallylacetamide,
Maleic hydrazide.

Mixture in the ratio of 1: 2 to 10: 1, preferably 1: 1 to 5: 1.

Inorganic and mixed inorganic-organic salts

The following salts can be used with 3- (o-fluorophenyl) -1-methylurea be mixed in the proportions given below:

A. Calcium propylar sonate,
Disodium monomethylarsonate, octyldodecylammoniummethylarsonate, dimethylarsinic acid.

Mixing in the ratio of 1: 4 to 4: 1, preferably 1: 2 to 2: 1.

B. sodium arsenite.

Mixture in the ratio of 1: 5 to 40: 1, preferably 1: 4 to 25: 1.

C. lead arsenate,
Calcium arsenate.

Mixture in a ratio of 150: 1 to 600: 1, preferably 100: 1 to 400: 1.

D. Sodium tetraborate, hydrated, granulated, sodium metaborate,
Sodium pentaborate,
Polyboron chlorate,

unrefined borate rock, such as Borascu. Mixing in a ratio of 3: 1 to 1500: 1, preferably 6: 1 to 1000: 1.

E. ammonium thiocyanate.

Mixing in a ratio of 1:10 to 20: 1, preferably 1: 5 to 5: 1.

F. Sodium Chlorate.

Mixture in the ratio of 1: 1 to 40: 1, preferably 2: 1 to 20: 1.

G. Ammonium sulfamate.

Mixture in a ratio of 1: 1 to 100: 1, preferably 1: 1 to 50: 1.

Other organic herbicides

The following organic herbicides can also be mixed with 3- (o-fluorophenyl) -l-methylurea in the respective the following quantities can be mixed:

A. 5,6-Dihydro- (4A, 6A) -dipyrido- (1,2-A, 2 ', 1'-C) -

pyrazinium dibromide.

Mixing in a ratio of 1:20 to 16: 1, preferably 1: 5 to 5: 1.

B. 3-Amino-1,2,4-triazole.

Mixture in the ratio of 1:20 to 20: 1, preferably 1: 5 to 5: 1.

C. 3,6-endooxohexahydrophthalic acid. Mixing in a ratio of 1: 3 to 20: 1, preferably 1: 2 to 10: 1.

D. Hexachloroacetone.

Mixing in the ratio of 1: 2 to 16: 1, preferably 1: 1 to 8: 1.

5 6

E. Diphenylacetonitrile, 'All the above ratios relate to NjN-dimethyl-o ^ a-diphenylacetamide, the weight.
NjN-Di-n-propyl ^ o-dinitro- ^ trifluor- The agents according to the invention are in one

methylaniline, herbicidally effective amount applied directly to the soil

! ^, N-di-n-propyl- ^ o-dinitro-'i-methylaniline. 5 treatment applied before or after emergence

Mix in a ratio of 1:10 to 30: 1, or can be mixed intimately with the soil,

preferably 1: 5 to 20: 1. In the case of agricultural soils,

F. O- (2,4-dichlorophenyl) -O-methyl-isopropyl side-up of weeds before emergence or

phosphoramidothiat, shortly after emergence ^l / ₂ to 2 ¹ Z. ₄ kg active ingredient / ha

2,3,5,6-tetrachloroterephthalic acid, dimethyl ester. 10 on. For soil sterilization, the herbicide rate is

Mixing in a ratio of 1: 4 to 20: 1, pre-effective amount depending on the type of soil 4 to 45 kg / ha,

preferably 1: 3 to 51: 1. The preparation of the active ingredient according to the invention

G. 2,4-dichloro-4'-nitrodiphenyl ether. can be done as follows:

Mixing in a ratio of 1:10 to 30: 1, 15 g of o-fluoroaniline are preferably mixed with 7.67 g of methyl 1: 5 to 20: 1. 15 isocyanate and 150 ml of dioxane, evaporated after 3 hours

Substituted Uracile ^ ei ²⁵ ° ^{C the} ^ ung in vacuum a where a

". ,, "",. Mixture of an oil and a few white crystals

Of 3- (o-fluorophenyl) -l-methyl-urea can FER kbleibt _bac, the white crystals filtered off and washed

ner with substituted uracils in the subsequent _{them with chloroform and then ether} . The lagging

Proportions are mixed. _{> 20 remaining solids ;} the 3- (o-fluorophenyl) -l-methyl urine

A. S-Cyclohexyl-o-methyluracil, stoff, melts at 155.7 to 156.7 ° C.
S-cyclohexyl-o-ethyluracil,

3-Cyclohexyl-6-sec-butyluracil, Example 1

«JSSÄS," - ^E ™ - "" * - "-". ^ preparation has the following

S-Cyclohexyl-e-isopropyluracil, Composition:

S-bromo-S-seL-butyl-o-methyluracil, 3- (o-fluorophenyl) -l-methylurea .. 50%

S-chloro-S-sec-butyl-o-methyluracil, attapulgite clay 48%

S-bromo-S-tert.-butyl-o-methyluracil, dioctyl sodium sulfosuccinate 1%

S-chloro-S-tert-butyl-o-methyluracil, ₃₀ sodium lignosulfonate 1%

^This preparation is in a dosage of

3-sec-butyl-5 6-dimethyluracil, S-bromo-S-norbornylmethyl-o-methyluracil, S-nitro-S-sec-butyl-o-methyluracil, S-Cyclohexyl - ^ - dimethyluracil, S-bromo-S-cyclohexyl-o-methyluracil, ^ Chlor-S-phenyl-o-methyluracil

% £ S Γ2 S 2 T ^VO: ' ^VOr "

B. S-Cyclohexyl-S ^ -trimethyleneuracil, S-sec-butyl-S ^ -trimethyleneuracil, S-isopropyl-S.o-trimethyleneuracil, 3-isopropyl-5,6-tetramethyleneuracil, S-isopropyl-S ^ -pentamethyleneuracil. Mixing in a ratio of 1: 6 to 6: 1, preferably 1: 4 to 4: 1.

C. S-Cyclohexyl-S-bromuracil, 3-cyclohexyl-5-chloruracil, 3-isopropyl-5-bromouracil, 3-sec-butyl-5-bromouracil, S-sec-butyl-S-chloruracil.

Mixing in the ratio of 1: 6 to 6: 1, preferably 1: 2 to 2: 1.

D. S-isopropyl-l-trichloromethylthio-S-bromo-6-methyluracil,

S-CyclÖhexyl-l-trichloromethylthio-S-bromo-6-methyluracil,

S-sec-butyl-l-acetyl-S-bromo-o-methyluracil, S-isopropyl-l-acetyl-S-bromo-o-methyluracil, S-isopropyl-1-trichloromethylthio-S-chloro-6-methyluracil.

Mixing in the ratio of 1: 4 to 4: 1, preferably 1: 2, to 2: 1.

^{in FO} ™ ^{FROM Di} ^ ^itaria «Ρ-JungemSorghum halepense, Richardia scabra and annual Ipomoea. _{The groove plant shows} ^J _{in n} * _rmal £ growth.

Example 2

3- (o-Fluorph _e n _y l) -l-methyl-urea 80% ..

Alkyl naphthalene sulfonate, sodium salt .... 2% Partially desulfonated sodium

Hgnine sulfonate 2%

Synthetic, fine silicon dioxide .. 8%

Kaolin-1 on 8/0

The preparation is mixed and finely ground (hammer mill of the Micropulverizer type) and then ground again on an air mill until the grain size is essentially all of the particles below 10 microns.

The preparation is before emergence by means of a spray device arranged on a tractor Applied to a freshly tilled potato field at a dosage of 1.7 kg active ingredient / ha. the Potato plants emerge with a good stand and result in an excellent

* nete fruit. Weeds such as Setaria faberii, Echinochloa crusgalli, Digitaria sp., Abutilon theophrasti medio and Amaranthus sp. germinate normally, but are subject to the effects of the chemical within a few days.

Example 3

3- (o-fluorophenyl) -l-methylurea .. 80%

Attapulgite clay 18%

Dioctyl Sodium Sulphosuccinate 1%

Sodium lignosulfonate 1%

11.3 kg of this preparation are suspended in 1511 Water and at the beginning of the growing season brings the suspension to an industrial site-like outdoor storage area 0.4 hectares in size. A mixed stand of weed-like vegetation, including Digitaria sp., Setaria lutescens, Potentilla anserina, Brassica kaber, Rudbeckia, Polygonum and Ipomoea come to the Germinates, but dies within 10 days.

Example 4

The superior activity of the compound according to the invention can be seen from Tables I and II below 3- (o-fluorophenyl) -l-methylurea (compound 1) versus the known herbicides

l- (m-Fluorophenyl) -3-methylurea (Compound 2, U.S. Patent 2,655,447, column 3, line 23) and l- (o-chlorophenyl) -3-methylurea (compound 3).

The stated test values are grades from a rating system ranging from 0 to 10. 0 means no visible reaction and 10 means that all treated plants died.
Table I shows that the agent according to the invention

ίο is already effective in considerably smaller quantities, than the known agent 2, but has the same selectivity in maize. Table II shows that the invention In contrast to active ingredient 3, agent is suitable for selective use in beans.

Table I.

Stanton Ground
Planting depth S

ε LB / A C.
flj 1λ G • I Echinochloa 0.634 cm (1/4 ") Setaria, fox tail
(G. Foxtail) Amaranthus
(Pigweed) mustard
(Mustard) Convolvulus I arvensis L.
(Bindweed) J S. (Chickweed) 2.54 cm (I ") Corn
(Corn) 3 1/8 ■>. I (Bermuda grass 3 0 10 10 5 ^ - CJ
CCf '3 0 '• 3 1/4 Cynodon dact
(L.) Pers. O 7th 10 10 7th Stellaria medi
Cyril, birds 0 Application before 1
3
cn
-8th
CD 1/2 9 "« * 4th 9 10 3 7th 0 the emergence
link Sandy soil 2 9 Digitaria spp.
(Crabgrass) (Barnyard grass 9 9 10 10 9 Avena fatua
(Wild Oats) 5 Connection 1 9 7th 10 0 Sandy soil 9 9 10 4th Connection 2 9 2 9 7th I crusgalli 5 Lolium multif
Lam.
(Ryegrass) 5 3 6th 3 4th 4th 0

Table II
Treated plants

Lb / A After emergence Sorghum
halepense
(Johnsongrass) Digitaria spp.
(Crabgrass)
i Digitaria spp.
(Crabgrass) Echinochloa
crusgalli
(Barnyard grass) Sorghum Before the emergence Avena fatua
(Wild Oats) Cassiatoria Ipomoea
pandurata (L.)
(Morning Glory) mustard
(Mustard) radish
(Radish) Marigold
(Marigold) Dock
(dock) Bean
(bean) 1 cotton 1 0 10 4th 3 4th 10 10 10 10 10 10 4th Connection 1 1/2 2 1 0 10 2 0 0 3 10 10 5 5 10 2 1/4 2 0 0 0 0 0 0 0 0 10 0 0 0 • 0 1/8 2 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 7th 10 10 10 10 10 10 10 10 10 10 10 10 Connection 3 1/2 5 2 2 10 10 10 10 10 10 10 10 10 10 10 1/4 5 1 1 10 10 8th 10 10 10 10 10 10 10 10 1/8 3 1 0 10 10 9 10 10 10 10 10 .: 10 10 10 2

309 581/423

Claims (1)

Claim: Weed control products, especially for weed control in cotton and potato plantations, characterized by a content of 3- (o-fluorophenyl) -l-methylurea as an active ingredient.