DE2900768A1 - LIQUID HERBICIDALS, EMULSIBLE IN WATER - Google Patents

Description

29007

S.I.P.C.A.M. Society Italiana Prodotti Chimici I 7711.

e per 1'Agricoltura Milano SpA, - ^1o " ^Jan * ¹⁹⁷⁹

Wa / Kdg I - 2o 136 Milan

Liquid herbicidal compositions which can be emulsified in water

Not always has liquid, water-emulsifiable herbicidal compositions which fully comply with the prior art because many herbicidal mixtures have a very low solubility in numerous solvents, which is why you often only liquid herbicidal compositions with low concentration of active substance with a high proportion of the solvent, which is very expensive. Sometimes such liquid herbicidal compositions with a low concentration of active substance and a high content of solvent, if they are to be used as selective herbicides for agricultural crops, are also phytotoxic because of the intolerance of the crops to high doses of various solvents.

Such difficulties are even greater when you are fluent Wants to produce herbicidal agents based on more than one active substance that is different in terms of physics and chemistry Possess properties.

90982 9/0738

⁸ 290076B

The aim of the invention is to emulsify liquid ^ in water

bare herbicidal agents based on more than one active Substance to provide a sufficient concentration of active Substance and an acceptable amount of solvent, so that they completely meet technical and economic standards correspond.

The liquid herbicidal compositions according to the invention therefore contain Mixtures of already known herbicidally active substances belonging to the compound classes of the substituted dinitroanilines and / or include substituted ureas and / or substituted s-triazines, in the presence of suitable solvents, and their physicochemical properties enable the production of liquids Means of a certain composition and concentration. Of course Suitable emulsifying agents can also be added.

It has now been found that liquid herbicidal compositions with superior properties can be prepared by mixing the following compounds with one another, with at least two active herbicidal substances belonging to different chemical compound classes being present:
a) one or more substituted dinitroanilines of the formula

L L ..

909829/0738

29007

worl.n R _{1 is} a hydrogen atom or an alkyl, alkoxy or alkyl thio group with 1 to 4 carbon atoms or a radical of the formula

^N \

^R 6

is ι R ₂ ,, R ,, R (- and R _ß a hydrogen atom, an alky! group with 1 to 4 carbon atoms _r an alkeny! group with 2 to 4 carbon atoms, an alkoxy or alkylthio group with 1 to 4 carbon atoms ,, is an alkylsulfonyl or alkylsulfinyl group or a radical of the formula - SO ₂ -NH ₂ , or -SO ₂ -NS- (CH ₃ ) -, the hydrogen atoms in all of the groups mentioned optionally with halogen atoms or with hydroxyl,. Cyano or azido groups can be substituted? R _{4 is} hydrogen , a trihalomethyl group, an alkyl group with 1 to 4 carbon atoms, an alkeny group with 2 to 4 carbon atoms, an alkoxy or alkylthio group with 1 to 4 carbon atoms or an alkylsulfony! group, one

-SO-N '

R ₇ alkylsulfinyl group or a radical of the formula /

where R ₇ and R 1 are hydrogen, an alkyl group with 1 to 4 carbon atoms, an alkeny group with 2 to 4 carbon atoms, a radical of the formula -SO ₂ -NS- (CH ₃ J ₂ , a haloalkyl group or a Cycloalkyl group with 3 to 6 carbon atoms or a radical of the formula " ^ci mI Jl

or “when two nitrogen atoms are adjacent, they share one

-4-

909829/0738

29007S8

heterocyclic ring (florpholine, piperazine or piperidine ring) mean;

and or

b) one or more substituted ureas of the formula

RR ₁ R ₀

I II ^1/2
(II) ANCN-

^R 3,

wherein A is a radical of the formula

ⁿ "^ c Vv

may be, in which X is a hydrogen or halogen atom or an alkyl, alkoxy, alkylthio or haloalkvlthio group with 1 to carbon atoms, an alkenyl or alkynyl group with 2 to 4 carbon atoms, a trihalomethyl group, trihalomethylthio group or a radical of the formula -OCF ₂ -CHF ₂ and η one

Value from ο to 3 can flash,

(Y)
or A is a group of the formula

denotes in which Y is a hydrogen or halogen atom or an alkyl group having 1 to 4 carbon atoms and η can have a value from ο to 2; R can be a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, an alkoxyalkyl group with 2 to 6 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms; R ₁ denotes an oxygen or sulfur atom, R denotes a hydrogen atom or an alkyl group with 1 to 4 carbon atoms and R ₃ denotes an alkyl or alkoxy group with 1 to 4 carbon atoms or an alkenyloxy group with 2 to 4 carbon atoms

909829/0738

290076

atoms means;
and or

c) one or more substituted s-triazines of the formula

N '

ν Ι

NC. CN
Y ^ NZ ₂

where X is a radical of the formula S-CH ₃ , -S-CH ₃ -CH ₃ or -OCH ₃ , Y is an alkyl group with 1 to 4 carbon atoms or dicyclopropylmethyl, Z _{1 is} a hydrogen atom or an alkyl group with 1 to 4 Carbon atoms, Z_ denotes an alkyl group with 1 to 4 carbon atoms, the cyclopropylmethy group or a

CH

Group of formula 1 3. ,. .

-OC-CN ^eae '

CH ₃

d) a solvent of the type de * "dialkyl or alkyl formamides, such as for example dimethylformamide, diethylformamide or another Alkylformamide.

The dialkyl or alkyl formamides mentioned, in particular dimethylformamide, can be used in the herbicidal compositions according to the invention in an amount of 1 to 90% by weight, depending on the type of herbicidal desired Agents are used and prove to be unexpectedly effective for obtaining liquid herbicidal agents that contain significant amounts of at least two active substances, which belong to the herbicidal chemical classes that have the above formulas ..

909829/0738

-y-

Of course, other non-phytotoxic auxiliary solvents can also be used be present, such as aromatic, aliphatic, cycloaliphatic and other polar solvents / such as dimethyl sulfoxide or N-methyl-pyrolidone, provided they are with each other are miscible and compatible, as well as other active herbicidal substances or Coadiuvantien, such as paraffinic or io ^ sparaffinic mineral oils and suitable surface-active or Emulsifiers, provided that only aqueous emulsions are obtained that are well balanced in their hydrophilic-hydrophobic balance are.

Aromatic hydrocarbons, the come from petroleum or tar from fossil coals, are used, also partially mixed with aliphatic or cycloaliphatic hydrocarbons, such as naphtha or kerosene, and also xylenes, toluenes and halogenated derivatives, alkylbenzenes and mixtures thereof, alkylnaphthalenes or tetra- or decahydronaphthalene or optionally cycloaliphatic hydrocarbons, further mixtures with aliphatic Solvents or, in particular, mixtures with other polar solvents, such as dimethyl sulfoxide or N-methylpyrolidone; or also alcohols or with alkyl acetates of the n-butyl acetate type or Glycol ethers, such as ethylene glycol inonoethyl or diethyl ether, and the acetates thereof, or ketones such as cyclohexanone. The content of active herbicidal substance on the basis of the substituted Dinitroaniline and / or ureas and / or s-triazines and optionally other active substances can vary within relatively wide limits, but is generally 5 to 75% (w / v)

-7- 909829/0738

# 5

with the range from Io to 50% (w / v) being preferred. The weight ratio between substituted dinitroaniline and substituted urea and / or substituted s-triazine can vary between 1: 2o and 2os1, but is preferably between 8s1 and 1s8 and that between urea and substituted ^s- triazine can vary between 10sl and 1s1o and is preferably between 4: 1 and 1s4. These solutions can be used in the form of an aerosol or of 'powdered compositions in the form of small droplets with the aid of suitable equipment for application from the air or from the ground »

To get these solutions in water for spraying on the ground or to emulsify the cultures using suitable equipment that works from the ground or from the air, in order to make them uniform to distribute, it is necessary to add suitable emulsifying agents, which are well balanced in their hydrophilic and hydrophobic properties in relation to the type of solution to be emulsified are, with compounds that are completely anhydrous and free from contamination by alcohols and polyalcohols, to be favoured. Such emulsifiers are generally made from mixtures of surface-active anionic and nonionic Substances formed, with an optimal balance between the hydrophobic and hydrophilic properties of the desired emulsion is adhered to and the optimal ratio between hydrophobic and hydrophilic emulsifying agents by means of simple laboratory methods Tests by a method well known to those skilled in the art are obtained in the following manner

9 0 9 8 2 9/0738 ~ ⁸ ~

You make two solutions that contain the same active substances and the same solvents, and then add the hydrophilic and the other solution to the hydrophobic emulsifier. The mixtures with different ratios between the two formulations and the emulsifying ability tests carried out with them in water allow the optimal ratio for a fully balanced balance between hydrophobic and to find hydrophilic properties. Examples of anionic surfactants usable in such emulsifiers are the alkali or alkaline earth salts of phenyl or naphthalene sulfonates, of fatty alcohol sulfonates, of sulfates of fatty acids or of sulfates of fatty alcohol glycol ethers, of polymethacrylates or methyl t_aurinates or other similar substances.

Examples of nonionic surface-active compounds used in such emulsifiers are used, the polyethoxylate condensates of octyl, isooctyl or nonylphenol, the polyethyloctylphenyl ether, Alkyl phenol polyglycol ethers, trialkyl phenyl polyglycol ethers or alkylaryl polyether alcohols, the condensates of fatty acids and alcohol ethylene dioxide, castor oil with ethylene oxide was polycondensed, fatty acids of alkanolimides that were polycondensed with ethylene oxide, the polycondensate of polyoxypropylene ethylene dioxide, Polyethylene alkyl ethers, alkyl alcohol polyglycol ether acetates, Sorbintan esters and other similar substances.

Examples of such emulsifying agents are also given in the publication "Mc Cutcheon's-Detergent and Emulsifiers", North America "

909829/0738 ^ _{TI = n}

ORIGINAL INSPECTED

/ 5 ° 2900753

Edition and International Edition, 1977 Annuals, Mc Cutcheon's

0
Publishing Co. Glen Rock / New Jersey (USA) included.

Examples of substituted dinitroanilines of the formula (x), which according to of the invention can be used are the following »

(11) N, N-di-n-propyl-4-trifluoromethyl-2 _i , 6-dinitroanilln (trifluralin)

(12) N-ethyl-N- (2-aethyl-2-oropyl) -4-trifluoromethyl-2,6-dinitroaniline (Etha-fluralin)

(13) 'N-Ethyl-N-n-butyl-2, 6-dinitro-p-toluidine (benf luralin)

(14) N, N-Di - n-propyl-4-isopropyl-2 _ir 6 - dinitroanilln (isopropaline)

(15) N- (2-chloroethyl) -N-n-propyl-4 »trifluoromethyl-2,6-dinitroaniline

(Flucloralin)

(16) N-ethyl-N-n-butyl-4-tri £ luoromethy1-2,6-dinitroaniline

(17) N-methyl-Nn-butyl-4-trifluoromethyl-2 _f 6-dinitroaniline

(18) N-Ethyl-N-2-methylallyl-4-trifluoromethyl-2,6-dinitroaniline

(19) N-ethyl-N-n-propyl-4-trifluoromethyl-2,6-dinitroaniline (Ho) N, N-di-n-propy 1-2,6-dinitro-p-toluidine

(111) N-Cyclopropylmethyl-N-n-propyl ~ 2,6-dinitro-p-toluidine (Profluralin)

(112) N-ethyl-N-tetrahydrofurfuryl-4-trifluoromethyl-2,6-dinitroaniline

(113) N- (4-trifluoromethyl-2,6-dinitrophenyl) pyrrolidine

(114) N- (4-trifluoromethyl-2, 6-dinitrophenyl) -piperidine

(115) N-sec-Butyl-4-tert-butyl-2,6-dinitroaniline

(116) N, N-di-n-propyl-4-methylsulfonyl-2,6-dinitroaniline (nitraline)

(117) N, N-di-n-propyl-4-sulfenylamido-2,6-dinitroaniline (oryzaline)

(118) N, N ™ di-n-propyl-4-, S, S-dimethylsulfylimino-2,6-dinitroan-iline

(Prosulfaline)

-1o-

"■ '"■'.'· I '^; -: 909829/0738 ORIGINAL INSPECTED

29UÜ7B-

(119) N, N-di-n-propyl-4-sulfamoyl-2,6-dinitroaniline

(120) NjN-Di-n-propyl- ^ - N-propylsulfamoyl- ^, 6-dinitroaniline

(121) N, N-di-n-propyl-4-N-ethyl-sulfamoyl-2,6-dinitroaniline

(122) N / N-Diethyl-S-methyl ^ -trifluoromethyl ^, 6-dinitroaniline

(Dinitramine)

(123) N- (1-ethylpropyl) -3,4-dimethyl-2/6-dinitroaniline (penoxaline)

Examples of herbicidally substituted ureas of the formula (II), which can be used according to the invention are:

(IH) N- (3,4-dichloropinyl) -N'-methyl-N'-methoxyurea f (Linuron)

(112) N- (4-chlorophenyI) -N ¹ -methy1-N'-methoxyurea (monolinuron)

(113) N- (4-bromophenyl) -N'-methyl-N'-methoxyurea (metobromuron)

(114) N- (3-Bromo-4-chlorophenyl) -N'-methy1-N'-methoxyurea

(Chlorobromuron)

(115) N- (4-methoxyphenyl) -N'-methy1-N ¹ -methoxyurea

(116) N- (4-ethoxyphenyl) -N'-methy1-N'-methoxyurea

(117) N- (4-Isopropylphenyl) -N'-methyl-N'-methoxyurea

(118) N- (3-chloro-4-methylphenyI) -N'-methy1-N'-methoxyurea

(119) N- (4-TrichloromethylphenyI) -N'-methy1-N'-methoxyurea (IHo) N- £ 3- (difluorochloromethoxy) phenylU-N ¹ -methy 1-N ¹ -methoxyurea f

(1111) N- (3,4-dichlorophenyl) -N-cyclopropylmethyl-N'-methy1-N ¹ -methoxyurea

1112) N- (3,4-dichlorophenyl) -N-cyclohex-1-eny1-N'-methyl-N'-methoxyurea

909829/0738

ORIGINAL INSPECTED

2 9 O ΰ 7 β ^

(ΙΙ13) N- 3-chloro-4- (difluorochloromethylthio) -phenyl -N-methyl-N'-methoxyurea

(1114) 3- (2-Benzothiazolyl) -1,3-dimethylurea (Metabenthiazuron)

(1115) N- (Phenyir _ff N'-diraethylthiourea

(1116) N- (4-chlorophenyl) -N °, N'dimethy! Thiourea

(1117) N- (4-bromophenyl) -N ', N'-dimethylthiourea

(1118) N- (3,4-dichloropKenyU-N ¹ , N'-dimethylthiourea

(1119) N- (3-trifluoromethyl) -M ', N'-dimethylurea (Fluometuron)

(1120) N- (3,4-dichlorophenyl) -N ^g , N'-dimethylurea (diuron)

(1121) N- (4-chlorophenyD-N ¹ , N'-dimethylurea (Monuron)

(1122) N- (4-methoxyphenyl) -N ', N'-dimethylurea (metoxuron)

(1123) N- (4-ethoxyphenyl) -N ', N'-dimethylurea (Etoxuron)

(1124) N- (3,4-Dichlornhenyl) -N ° -methyl-N-butyl-urea (Neburon)

(1125) N-phenyl-N ', N-dimethylurea (fenuron)

(1126) 3-Π ¹ * V, 2 \ 2 "-Tetraf (luoroethoxy-) phenyl-N , N-dimethylurea f.

Examples of herbicidal s -tiazines which can be used according to the invention of formula (III) are

(1111) 2-methylthio-4-ethylamino-6 = terto ° bi2tylamino-s-iriazine (Terbutryna)

(1112) 2-methylthio - ^ - ethylamino-6-sec = butylamino-s = triazine (See »butryna)

(1113) 2-methylthio "4-ethylamino-6 = isopropylamino- ^s ° triazine (Ametryna)

(1114) 2-methylthio-4 _J, 5-bis-ethylaraino-s "triazine (Symetryna)

-12-

9 O 9 8 2 9/0 7 3 8 ORIGINAL INSPECT ^ *

29007 * 3

(1115) 2-methylthio-4,6-bis-isopropylamino- s-triazine (Prometryna)

(1116) 2-ethylthio-4,6-bis-isopropylamino-s-triazine (Dipropetryna)

(1117) 2-Methylthio-4-methylamino-6- (1,2-dimethyl-N-propylamino) -s-triazine (Dimetametryna)

(1118) 2-Methylthio-4-ethylaInino-6- (2-methylpropionitrilamino) -s T riazin (Cyanatryna)

(1119) 2-Methylth 10-4-CyClOPrOPyIaItIInO-O- (2-methylpropionitrilamino) -s-triazine (Cycletryna)

(11110) 2-Metb-oxy-4-ethylamino-6-tert-butylamino-T-triazine (Terbumetone)

(11111) 2-Methoxy-4-ethylamino-6-sec-butylamino-s-triazine (Secbumeton)

(11112) 2-Metb-oxy-4-ethylamino-6-isobutylamino-s-triazine (Isobumetone).

According to the solutions of the herbicides based on substituted dinitroanilines and / or ureas and / or s-triazines According to the invention, as already mentioned, further herbicides can be dissolved or added in suspension, and if these other herbicides Herbicides are insoluble in the solvents which can be used according to the invention the particles of these substances in suspension must be extremely fine with a diameter of less than 5 microns and if possible below 2 microns and kept in solution by suitable Coadiuvantien so that water-dispersible flowable pastes are formed.

9 0 9 8 2 9/0738 ORIGINAL INSPECTED

| 4 | 2300768

There are also additions of cpadiuvantienj, penetrants, Adhesives and various surface-active agents possible, to improve the properties of the solutions mentioned »

The herbicidal solutions or suspensions according to the invention are prepared in specially designed mixing devices and must be used either before sowing with or without any possible introduction into the soil or after sowing and in this case either before the cultures germinate from the soil or after germination, depending on the type of agent used.

The following examples serve to further explain the invention, without restricting them »

Formulation examples

The compounds listed below are used in a mixer dissolved with shaking until liquid, stable and homogeneous herbicidal compositions according to the invention are obtained.

Formulation 1 24 kg Formulation 2 24 kg Connection (11) 12th kg Connection (11) 16 kg Compound (III) 12th kg Compound (II24) 2o kg Dimethylformamide 46 kg Dimethylformamide 34 kg Xylene Xylene Emcol N 3ooB + 1
Emcol N 5ooB 2) j 6th kg Emcol N 3ooB + Λ .6 kg Emcol N 5ooB 2) J.

1oo kg 1oo kg

9098 2 9/0738

Formulation 3 24 kg Connection (11) 6th kg Connection (IH) 6th kg Compound (III1) 15th kg Dimethylformamide 41 kg Xylene Triton X 151+ Λ 8th kg Triton χ 171 1) J.

(H 290Ü 51 + 24 kg (II 71 1 9 kg Formulation 4 ) 6th kg link 1) 12th kg link (III1) 41 kg link Dimethylformamide Xylene 8th kg Triton X 1 Triton X 1

100 kg

100 kg

Formulation 5 24 kg Formulation 6 2o kg Connection (11) 8th kg Connection (H) 8th kg Compound III) 8th kg Connection (IH) 8th kg Compound III5) 12th kg Compound (III6) 12th kg Dimethylformamide 4o kg Dimethylformamide 44 kg Xylene Xylene Atlox 4855 B +}
Atlox 4851 B 3) J. 8th kg Emcol N 3oo B + ~) 8th Emcol N 5oo B 2) f

100 kg

100 kg

Formulation 7 I. 1 24 kg Formulation 8 ORIGINAL 24 kg -15 Connection (11) 12th kg Connection (11) 6 kg INSPECTED Compound (114] 12th kg Connection (114) 6 kg Dimethylformamide 46 kg Compound (III1) 12 kg Xylene Dimethylformamide 44 kg Emcol N 300 B + 6th kg Xylene Emcoi N 5oo B 2) 1oo kg Triton X 151+ "")
Triton X 171 1)} 8 kg 100 kg 909829 / 0738

Formulation 9

link (ID 51+ ^ 24 kg link (IH) 71 1) \ 6th kg link (III6) 6th kg Dimethylformamide 1o kg Xylene 48 kg Triton X 1 Triton X 1 6th ^k 9

24 kg Formulation 1o 12th kg Connection (11) 12th kg Compound (III1) 44 kg Dimethylformamide Xylene 8th kg Triton X 151 + J Triton X 171 1) \

100 kg

too kg

Formulation 11 24 kg Connection (H) 1o kg Compound (III6) 1o kg Dimethylformamide 48 kg Xylene Triton X 151 +>
Triton X 171 1) J. 8th key

Formulation 12

Connection (12) 24 kg Connection (111) 12th kg Dimethylformamide 12th kg Xylene 46 kg Emcol N 3oo B 4- - \ Emcol N 5oo 2)? 6th kg

loo kg 100 kg

Formulation 13 24 kg Connection (12) 16 kg Connection (1124) 25th kg Dimethylfo rmami d 29 kg Xylene Emcol N 3oo B + - \ 6th kg Emcol N 5oo B 2) {

100 kg

909829/0738

Formulation 14 24 ) kg Connection (12) 6th ) ⁸ kg Connection (111) ) 8th 1oo kg Compound (III1 15th -K kg Dimethylformamide 39 kg Xylene Triton X 151 + kg Triton X 171 1) kg INSPECTpn ORIGINAL

Formulation 15 Compound (12) Compound (IH) Compound (III1) dimethylformamide xylene

Triton X 151 + Triton X 171 1)

¹ X-

24 kg 9 kg 6th kg 12th kg 41 kg 8th kg

29ÜU7

100 kg

Formulation 16
Connection (12)
Connection (IH)
Compound (III5) dimethylformamide
Xylene

Atlox 4855 B +
Atlox 4851 B 3)

2o kg 6th kg 6th kg 1o kg 52 kg 6th kg

100 kg

Formulation 17 Compound (12) Compound (IH) Compound (III6) dimethylformamide xylene

Atlox 4855 B + Atlox 4851 B 3)

kg Formulation 18 24 kg 2o kg Connection (12) 12th kg 6th kg Compound (III1) 12th kg 6th kg Dimethylformamide 46 kg 1o kg Xylene 5o Triton X 151 +} 6th kg kg Triton X 171 1) λ 1oo kg 8th

100 kg

Formulation 19 24 kg Formulation 2o 24 kg Connection (12) 1o kg Connection (14) 12 kg Compound (III6) 1o kg Connection (113) 15 kg Dimethylformamide 5o kg Dimethylformamide 43 kg Xylene Xylene Atlox 4855 B +>
Atlox 4851 B 3) \ 6th ^k 3 Triton X 151+) 6 kg 1oo kg Triton X 171 1) J. 100 kg -17- 9 09829 INSPECTED ¹ ° ^{7 3 8} ORIGINAL

Formulation 21

Connection (111)

Connection (111)

Dimethylformamide

Xylene

Emcol N 300 B +

Emcol N 5oo B 2)

kg "U 2900 7B8 ) β kg kg Formulation 22 kg 2o kg Connection (111) 2o kg 1o kg Compound (II24) 12th kg 1o Dimethylformamide 2o 54 Xylene 42 Emcol N 3oo B + ' 6th Emcol N 5oo B 2)

loo kg 100 kg

Formulation 23 24 kg Connection (111) 12th kg Connection (114) 1o kg Dimethylformamide 46 kg Xylene Triton X 151 + \ 8th ^k 57 Triton X 171 1)>

Formulation 24 2o kg Connection (111) 1o kg Connection (ΙΪΙ5) 12th kg Dimethylformamide 5o kg Xylene Atlox 4855 B + "j 8th kg Ätlox 4851 B 3) T

1oo kg 1oo kg

Formulation 25 2o kg Connection (122) 1o kg Connection (111) 6th kg Dimethylformamide 58 kg Xylene Emcol N 3oo B + Λ 6th Emcol N 500 B 2) j

Formulation 26 2o kg Connection (122) 12th kg Compound (III6) 1o kg Dimethylformamide 5o kg Xylene Emcol N 3oo B + χ 8th kg Emcol N 5oo B 2) (

1oo kg 1oo kg

-18-

909829/0738

ORIGINAL INSPECTED

19th

29007-3

Formulation 27 2o kg Formulation 28 2o kg Connection (123) 1o kg Connection (123) 12th kg Connection (111) 12th kg Compound (III6) 1o kg Dimethylformamide 5o kg Dimethylformamide 5o kg Xylene Xylene Triton X 151 + ν
Triton X 171 1) j 8th kg Emcol N 3oo B + \ 8th kg Emcol N 5oo B 2)]

100 kg

100 kg

Formulation 29 2o kg Formulation 3o 2o kg Connection (123) 1o kg Connection (123) 5 kg Connection (114) 1o kg Connection (111) 5 kg Dimethylformamide 54 kg Compound (III1) 12th kg Xylene Dimethylformamide 52 kg Triton X 151 + * \
Triton X 171 1) J. 6th kg Xylene 1oo kg Atlox 4855 B +)
Atlox 4851 B 3) J. 6th kg

100 kg

100 kg

Formulation 31 2o kg Formulation 32 Ϊ 2o kg Connection (123) 4th kg Connection (123) 1o kg Connection (114) 6th kg Compound (III6) 12th kg Compound (III1) 12th kg Dimethylformamide 5o kg Dimethylformamide 52 kg Xylene Xylene Emcol N 300 B + 8th kg Atlox 4855 B + "\
Atlox 4851 B 3) J. 6th kg Emcol N 5oo B '2) 1oo kg

-19-

909829/0738

ORIGINAL INSPECTED

29007 * 3

Formulation 33

Connection (123) 2o kg

Compound (III5) to kg

Dimethylformamide 12 kg

Xylene 52 kg Atlox 4855 B + ■ \ Atlox 4851 B 3) J 6 kg

too kg

1) Rohm & Haas Co. - USA

2) Witco Chemical Co. - USA

3) I.C.I. Co. UK

annotation

The emulsifier pairs are used in a proportion this on a case-by-case basis depending on the nature of the impurities active substances and solvents according to those already described The procedure is to establish an optimal balance between the hydrophilic and hydrophobic properties of the emulsions to obtain.

The herbicidal compositions according to the invention can be used selectively Weed control can be used in arable crops as described below:

a> some herbicidal agents, such as those of the formulations 1,2,3,4, 7,8,9, to, 12,13,14,15,29,3o and 31 can be used to kill weeds in various crops, such as of wheat and different types of grain (barley, rye, oats, rice or maize ) on the top

'-2o-

- JU, 29007S3

can be used either as pre- or post-emergence herbicides without having to be worked into the surface layer of the soil in order to avoid phytotoxic phenomena.

b) Other herbicidal agents can be used for weed control in legumes, such as peanuts or soy »or in umbels such as carrots, after prior distribution on the surface of the soil and working into the soil to a depth of 2 to 4 ent can be used, such as the formulations 1,2,7,8,12,13,21,22,23,27 and 29.

c) Still other herbicidal gowns can be used to eradicate Etakrautvertilg in cotton crops, where they are distributed on the soil surface and ire the soil to a depth of 2 to 4 cm, such as the formulations 1,2,9, To, 11,12 , 21,22, 26, 27 _r 2S and 32.

d) Other herbicides can always nacfi prior incorporation _r in the bottom surface but to other crops such as sunflowers, applied _f such as the formulations 1,2,5,12,13, 17,24, and 33rd

e) The formulation 2o can also be applied to tobacco, namely in before; transplant into the soil * form.

Further uses are for the herbicidal gowns according to the invention for the purposes mentioned and described in the examples addition ssSgl £ ch \.

' V

S09829 / 0738

ORIGtNAL INSPECTED

Claims (9)

I 7711 1ο. Jan. 1979 Wa / Kdg claims 1.Liquid herbicidal agent * that can be emulsified in water contains:
a) one or more substituted dinitroanilines of the formula -2- 2 "3 909829/0738 ORIGINAL INSPECTED wherein R- is a hydrogen atom or an alkyl, alkoxy or alkyl thio group having 1 to 4 carbon atoms or a radical of the formula is; R ~ _# R-, R (- and R _fi a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkoxy or alkylthioorupne with 1 to 4 carbon atoms, an alkylsulfonyl or alkylsulfinyl group or a radical of the formula - SO ₂ -NH ₂ , or -SO ₂ -NS- (CII ₃ J ₂ , where in all of the groups mentioned dip hydrogen atoms can optionally be substituted with halogen atoms or with hydroxyl, cyano or azido groups; R. Viasserstoff , a trihalomethyl group, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkoxy or alkylthio group having 1 to 4 carbon atoms, or an alkylsulfonyl group -SO-N R ₇ alkylsulfinyl group or a radical of the formula / ^R 8 where R ₇ and R "are hydrogen, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, a radical of the formula -SO ₂ -NS- (CH ₃ ) -, a haloalkyl group or a cycloalkyl group with 3 to 6 carbon atoms or a radical of the formula ~ ^CH v | l || or, if two nitrogen atoms are adjacent, they share one -4- . _{: i;} .. ,,., 909825 / O738 BAD ORiGiNAL 29OiJT -J heterocyclic ring (morpholine, piperazine or piperidine ring) mean; and or b) one or more substituted ureas of the formula RR ₁ R ₀ I II ^1/2
(ZI) ANCN- wherein A is a radical of the formula may be, in which X is a hydrogen or halogen atom or an alkyl, alkoxy, alkylthio or haloalkylthio group with 1 to carbon atoms, an alkenyl or alkynyl group with 2 to 4 carbon atoms, a trihalomethyl group, trihalomethylthio group or a radical of the formula - OCF.-CHF, and η can flash a fourth from ο to 3,
or A is a group of the formula denotes in which Y is a hydrogen or halogen atom or an alkyl group having 1 to 4 carbon atoms and η can have a value from ο to 2; R can be a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, an alkoxyalkyl group with 2 to 6 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms; R ₁ denotes an oxygen or sulfur atom, R ~ denotes a hydrogen atom or an alkyl group with 1 to 4 carbon atoms and R. an alkyl or alkoxy group with 1 to 4 carbon atoms or an alkenyloxy group with 2 to 4 carbon atoms 9 09829/0738 ORlGiNAL INSPECTED 2300768 atoms means;
and or c) one or more substituted s-triazines of the formula u NNZ ₁ (in) ^H ^ ' ^{u 7l} NZ ₂ wherein X is a radical of the formula S-CH ₃ , -S-CH ₂ -CH ₃ or -OCH ₃ , Y is an alkyl group with 1 to 4 carbon atoms or dicyclopropylmethyl group, Z _{1 is} a hydrogen atom or an alkyl group with 1 to 4 carbon atoms , Z _{3 is} an alkyl group with 1 to 4 carbon atoms, the cyclopropylmethyl group or a group of the formula CH ₃ -O-C-CN means; Ah ₃ d) a solvent from the group of dialkyl or alkyl formamides. 2. Means according to claim 1, characterized in that the solvent Is dimethylformamide. 3. Agent according to claim 1, characterized in that it also contains non-ionic and / or anionic emulsifiers. -5- 909829/0738 290076a - 4. Agent according to one of claims 1 to 3, characterized in that that it also contains aromatic, aliphatic or cycloaliphatic hydrocarbons or other polar solvents. 5. Agent according to one of claims 1 to 4, characterized in that that it contains further herbicides in solution or suspension. 6. Agent according to one of claims 1 to 5, characterized in that that it contains the active substances in an amount of 5 to 75% and especially 10 to 5o% (w / v). 7. Agent according to one of claims 1 to 6, characterized in that that the weight ratio between dinitroaniline and urea and / or s-triazine is 1: 2o to 2os1 and in particular 8: 1 to 1: 8 amounts to. 8. Agent according to one of claims 1 to 6, characterized in that that the weight ratio of urea to triazine 1: 1o to 1o: 1 and in particular 1: 4 to 4: 1. one of the 9. Process for the preparation of the herbicidal compositions according to / claims 1 to 8, characterized in that the active substances are mixed with solvents or emulsifiers in a suitable device and various Coadiuvantien mixed. 909829/0738 29007 * 8 1o. Weed control methods in agricultural crops by distributing the agent according to one of claims 1 to 8 either before sowing, optionally with incorporation of the Means in the soil or after sowing the culture before or after its germination. 9 09829/0738 BADORIQiNAi