DE4237920A1 - 3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape - Google Patents

Abstract

3-Aryluracil derivs. of formula (I) and their agrochemically acceptable salts (if R is H) are new. W is -N(R1)CO- or -N=C(OR11)- bonded to the ring N via C; R is H, 1-4C alkyl, 1-4C haloalkyl, 3-4C alkenyl or 3-4C alkynyl; R2 is halogen or CN; R3 is H or halogen; R4 is H, halogen or 1-4C alkyl; R5 is 1-4C alkyl or 1-4C haloalkyl; or R4 and R5 together form -(CH2)n-; n is 3-4; R11 is 1-4C alkyl, 3-4C alkenyl or 3-4C alkynyl; Q is -CR6R7R8; R6 and R7 are each H, 1-8C alkyl, 3-7CV cycloalkyl or 3-7C cycloalkyl(1-4C)alkyl; R8 is halogen or X1R9; X1 is O, S(O)m, OSO2 or SSO2; R9 is H, 1-5C alkyl, 1-4C alkoxy(1-4C)alkyl, 3-8C cycloalkyl, 3-8C cycloalkyl(1-4C)alkyl, 1-5C haloalkyl, 2-5C alkenyl, 2-5C alkynyl, opt. substd. aryl, opt. substd. benzyl or -C(=X2)R10; X2 is O or S; R10 is H, 1-5C alkyl, 1-4C alkoxy(1-4C)alkyl, 3-8C cycloalkyl, 3-8C cycloalkyl(1-4C)alkyl, 1-5C haloalkyl, 2-5C alkenyl, 2-5C alkynyl, 1-5C alkoxy, 1-4C alkoxy(1-4C)alkoxy, 1-5C haloalkoxy, 2-5C alkenyloxy, 3-5C alkynyloxy, 1-5C alkylthio, 3-5C alkenylthiom, aryloxy, arylthio, benzyloxy, benzylthio, aryl or benzyl (these last 6 gps. opt. substd.); and m is 0-2; provided that in X1R9, if R9 is H or -C(=X2)R10, X1 is O or S. USE/ADVANTAGE - (I) are herbicides effective against weeds, including grasses. They are effective against e.g. Arenafatua, Echinochloa crus-galli, Sorghum halepense, Chenopodium album, etc. in crops such as rice, wheat, maize, soya, rape and cotton. Suitable amts. for use are 1g-3kg esp. 10g-1kg/ha, esp. 10-100 g/ha for pre-emergence use and 100-1000 g/ha post-emergence. (I) can also be used as desiccants to facilitate harvesting in crops such as cotton, potato and rape.

Description

The present invention relates to novel 3-aryluracils of the formula I.

wherein
-W- the group

wherein the bond to the ring nitrogen atom is via the C atom;
R₁ is hydrogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃ or C₄ alkenyl or C₃ or C₄ alkynyl;
R₂ is halogen or cyano;
R₃ is hydrogen or halogen;
R₄ is hydrogen, halogen or C₁-C₄-alkyl;
R₅ is C₁-C₄ alkyl or C₁-C₄ haloalkyl; or R₄ and R₅ together are - (CH₂) _n -;
n is the number 3 or 4;
R₁₁ is C₁-C₄ alkyl, C₃ or C₄ alkenyl or C₃ or C₄ alkynyl; and
Q the group

means
wherein R₆ and R₇ are independently hydrogen, C₁-C₈-alkyl, C₃-C₇-cycloalkyl or C₃-C₇-cycloalkyl-C₁-C₄-alkyl;
R₈ is halogen or a group -X₁-R₉ (2) in which
X₁ is oxygen, -S (O) _m -, -OSO₂- or -S-SO₂-;
R₉ is hydrogen, C₁-C₅-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₅-haloalkyl, C₂-C₅-alkenyl , C₂-C₅ alkynyl, optionally substituted aryl, optionally substituted benzyl or a group

wherein
X₂ is oxygen or sulfur; and
R₁₀ is hydrogen, C₁-C₅-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₅-haloalkyl, C₂-C₅-alkenyl , C₂-C₅-alkynyl, C₁-C₅-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₅-haloalkoxy, C₂-C₅-alkenyloxy, C₃-C₅-alkinyloxy, C₁-C₅-alkylthio, C₃ -C₅-alkenylthio, or an optionally substituted aryloxy, arylthio, benzyloxy, benzylthio, aryl or benzyl radical;
m is the number 0, 1 or 2;
with the condition that in formula 2, if R₉ is hydrogen or the group

X₁ is oxygen or sulfur; and when R₁ is hydrogen is, even the agrochemically acceptable salts of compounds of formula I.

The inventive 3-acryluracils of the formula I in which the group -W- in the Amide Form Ia

or in the imino ether form Ib

present wherein R₁, R₂, R₃, R₄, R₅, R₁₁ and Q are the meanings given under formula I.  have, as well as the possible salts of these compounds, are herbicidally active and are useful as active ingredients of weedkillers. Thus, the The present invention also provides weed control compositions comprising the invention Compounds containing as active ingredients, process for preparing these compounds, and the use of such compounds or compositions for controlling of weeds.

Structurally similar herbicidally active 3-aryluracil derivatives are z. B. known from the EP-A 01 95 346, wherein uracils are disclosed with Q as carboxylic acid and ester groups; EP-A 02 55 047, in which uracils with Q as ethers, (thio) carbonyloxy and sulphonyloxy Groups are disclosed; and EP-A 02 60 621, in which uracils with Q as ether, Alkyl-carbonyloxy, alkoxy-carbonyloxy and alkoxycarbonyl groups disclosed become.

In the formulas I, Ia and Ib of the 3-aryluracils according to the invention, halogen means the definitions of the radicals R₂, R₃, R₄ and R₈ iodine, in particular fluorine, chlorine and bromine. The alkyl, alkenyl and alkynyl radicals R₁, R₄, R₅, R₁₁, R₁₂, and the corresponding as Substituents in Q suitable radicals R₆, R₇, R₉ and R₁₀, can be straight-chain or branched, and this also applies to the alkyl part of the haloalkyl, alkoxy, alkenyl and alkynyl groups. Examples of such alkyls are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl, examples of alkenyls being vinyl, Allyl, methallyl or but-2-en-1-yl and as examples of alkynyls are ethynyl, Propargyl, 1-methylpropargyl, but-2-yn-1-yl, but-3-yn-1-yl and pent-4-yn-1-yl. Alkenyl and alkynyl radicals having a chain length of two to four are preferred Carbon atoms. Alkoxy is for example methoxy, ethoxy, propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy or t-butyloxy; preferably methoxy, propyloxy and i-propyloxy, alkoxyalkyl in the definitions of the radicals R₉ and R₁₀ for example, methoxymethyl, methoxyethyl or ethoxyethyl. Alkylthio in the radical R₁₀ is for example, methylthio, ethylthio, propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio or t-butylthio, preferably methylthio, ethylthio or i-propylthio. A Haloalkyl group may have one or more (same or different) halogen atoms having as examples of a polyhalogenated alkyl group trifluoromethyl and pentafluoroethyl. In the coming into consideration as substituents Cycloalkyl radicals R₆, R₇, R₉ and R₁₀ are, for example, cyclopropyl, Cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. Under aryl in the radicals R₉ and R₁₀ is especially phenyl, these groups may be substituted  with 1 to 3 halogen atoms, C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy, C₁-C₃-Alyklthio, C₂-C₄-alkanoyl, C₂-C₄-alkoxycarbonyl, C₁-C₃-alkylsulfonyl, nitro and cyano.

The salts of the compounds of the formula I are, in particular, Alkali metal salts, e.g. For example, sodium and potassium salts; Alkaline earth metal salts, e.g. B. calcium and magnesium salts; Ammonium salts, d. H. unsubstituted ammonium salts and mono- or multi-substituted ammonium salts, e.g. Triethylammonium and methylammonium salts, as well as salts with other organic bases, eg. With pyridine.

The possible presence of at least one asymmetric carbon atom in the Compounds of formula I has the consequence that the compounds in optically active Single isomers, as well as in the form of racemic mixtures may occur. In the present invention are among the active ingredients of the formula I, both the pure to understand optical antipodes as well as the racemates. Unless specifically on the individual optical antipodes are those racemic mixtures Under the given formula to understand the specified manufacturing process arise. By the presence of any aliphatic C = C double bond can also geometric isomerism occur. In addition, in those compounds of Formula I, in which R₁ is hydrogen, does not rule out that the keto-enol Tautomerie

occurs. The formula I is all these possible isomeric forms, as well as mixtures thereof.

Among the compounds of formula I are the meanings of the following radicals particularly relevant:

a) R₁ is hydrogen, C₁-C₄-alkyl, C₃- or C₄-alkenyl, or C₃- or C₄-alkynyl, in particular methyl, allyl or propargyl; or and
b) R₂ is fluorine, in particular chlorine, bromine or cyano; or and
c) R₃ is hydrogen or fluorine; or and
d) R₄ is methyl, in particular hydrogen or fluorine; or and
e) R₅ is C₁-C₄alkyl, trifluoromethyl or pentafluoroethyl; or R₄ and R₅ together form an alkylene bridge, where n is the number 3 or 4; and
f) Q is the radical of the formula 1 in which R₆ is C₁-C₃alkyl, in particular hydrogen; and
R₇ is C₁-C₆-alkyl or C₅-C₆-cycloalkyl, in particular hydrogen, methyl, ethyl, isopropyl or cyclohexyl; and
R₈ is bromine or the group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m - or -OSO₂-; R₉ is C₁-C₃alkyl, C₁-C₃alkoxy-C₁- or C₂-alkyl, C₂- or C₃-alkenyl, C₃- or C₄-alkynyl, optionally substituted phenyl or benzyl; or R₉ is hydrogen or the group

when X₁ is oxygen or sulfur; X₂ is oxygen or sulfur; and R₁₀ is C₁-C₃ alkyl, vinyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₂ or C₃ alkenyloxy, C₃ or C₄ alkynyloxy, C₁-C₃ alkylthio or phenyl; m is the number 0, 1 or 2; or and
g) R₁₁ C₁-C₃-alkyl, allyl or propargyl, especially methyl.

Preference is given to the 3-aryluracil derivatives of the formula I in which R₁ is C₁-C₄-alkyl, C₁-C₄ haloalkyl, C₃ or C₄ alkenyl or C₃ or C₄ alkynyl; in particular wherein R₁ is methyl, allyl or propargyl; preferably R₁ is methyl.

Preference is likewise given to the 3-aryluracil derivatives of the formula I in which Q is the radical of the formula I where R₆, R₇ and R₈ are as defined for formula I; in particular wherein R₆ and R₇ independently, hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁- or -C₂-alkyl; R₈ is halogen or a group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m -, -OSO₂-; R₉ is hydrogen, C₁-C₃-alkyl, C₁- or C₂-alkoxy-C₁- or C₂-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁- or -C₂-alkyl, C₁-C₃-haloalkyl, C₃-C₅ alkenyl, C₃-C₅ alkynyl, substituted or unsubstituted aryl or benzyl, or a group

where R₁₀ C₁-C₅-alkyl, C₁-C₃-alkoxy-C₁- or C₂-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁- or C 2 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C alkenyl, propargyl, C 1 -C 3 -alkoxy, C₁-C₃-alkoxy-C₁- or -C₂-alkoxy, C₁-C₃-haloalkoxy, C₂- or C₃-alkenyloxy, C₃-C₅-alkynyloxy, C₁-C₃-alkylthio, C₃-alkenylthio, or an optionally substituted aryloxy, benzyloxy, arylthio, aryl or benzyl radical; m the Number 0, 1 or 2; with the condition that if R₉ is hydrogen or the group

X₁ is oxygen or sulfur; preferably, R₆ and R₇ are independently hydrogen, C₁-C₃ alkyl or C₃-C₆ cycloalkyl; R₈ is halogen or a group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m -, or -OSO₂-; m is the number 0,1 or 2; R₉ is hydrogen, C₁-C₃ alkyl, allyl, propargyl, optionally substituted aryl or the group

in which R₁₀ is C₁-C₃alkyl, C₁-C₃-haloalkyl, allyl, Propargyl, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₃-alkenyloxy, propargyloxy or C₁-C₃-alkylthio.

Particularly preferred are 3-aryluracil derivatives of the formula Ia, wherein R₁ is hydrogen, C₁-C₄-alkyl, C₃- or C₄-alkenyl or C₃- or C₄-alkynyl; R₂ is chlorine, bromine or cyano; R₃ is hydrogen or fluorine; R₄ is hydrogen, fluorine or methyl; R₅ is C₁-C₄ alkyl, trifluoromethyl or pentafluoroethyl; or R₄ and R₅ together are - (CH₂) _n -; and n is the number 3 or 4; and in which in particular R₁ is hydrogen, methyl, allyl or propargyl; R₂ cyano, chlorine or bromine; R₄ is hydrogen or methyl; and R₅ is methyl, trifluoromethyl or pentafluoroethyl.

Further, particularly preferred are 3-aryluracil derivatives of the formula Ib, wherein R₂ is chlorine, bromine or cyano; R₃ is hydrogen or fluorine; R₄ is hydrogen, methyl or fluorine; R₅ is methyl, trifluoromethyl or pentafluoroethyl; or R₄ and R₅ together are - (CH₂) _n -; n is the number 3 or 4; and R₁₁ is C₁-C₂ alkyl, allyl or propargyl; and in which in particular R₂ is chlorine; R₄ is hydrogen; R₅ is methyl, trifluoromethyl or pentafluoroethyl; and R₁₁ is methyl.

Very particular preference is given to 3-aryluracil derivatives of the formula I in which -W- group

means; R₁ is methyl; R₂ is cyano or chloro; R₃ is hydrogen or fluorine; R₄ is hydrogen or methyl; R₅ is methyl, trifluoromethyl, pentafluoroethyl; or R₄ and R₅ together are - (CH₂) _n -; n is the number 3; and Q the group

wherein R₆ and R₇ are independently hydrogen, C₁-C₅-alkyl or C₅- or C₆-cycloalkyl; R₈ is halogen or a group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m -, or -OSO₂-; R₉ is hydrogen, C₁-C₃ alkyl, allyl, propargyl, optionally substituted aryl or the group

wherein R₁₀ is C₁-C₃alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-alkenyloxy, propargyloxy or  C₁-C₃ alkylthio; and m is the number 0, 1 or 2.

Preferred individual compounds of the formula I are:
2-propanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl) ester,
Isobutyric acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro-methyl-1 (2H) -pyrimidinyl] -benzyl) ester,
(2-Chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl) -isopropyl ether,
(2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] benzyl) allyl ether, and
Methanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro-methyl-1 (2H) -pyrimidinyl] -benzyl) ester.

The inventive method for the preparation of the compounds of formula I and their salts is carried out in analogy to known methods and is characterized in that
a) for the purpose of producing those 3-aryluracil derivatives of the formula I in which R₁ is hydrogen, and optionally of metal salts of these compounds, a compound of formula IIa or IIb

wherein R₂, R₃ and R₅ have the meanings given under formula I; and R₄ 'is hydrogen, fluorine or C₁-C₄ alkyl; R₅ is C₁-C₄ alkyl; or R₄ 'and R₅ or R₅' together are - (CH₂) _n -, where n is the number 3 or 4; R₁₂ C₁-C₆-alkyl, preferably C₁-C₄-alkyl; and Q 'the group

wherein R₆ and R₇ are independently hydrogen, C₁-C₈ alkyl, C₃-C₇ cycloalkyl or C₃-C₇ cycloalkyl-C₁-C₄ alkyl; X₁ is oxygen, or -S (O) _m -; R₉ 'is hydrogen, C₁-C₅-alkyl, C₁-C₄-alkoxy. C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₄alkyl, C₁-C₅haloalkyl, C₂-C₅alkenyl, C₂-C₅alkynyl, optionally substituted aryl, optionally substituted benzyl; and m is 0, 1 or 2, with the proviso that when R₉ 'is hydrogen, X₁ is oxygen or sulfur, subject to cyclization by treatment with a base and optionally a resulting salt of the uracil derivative of formula IIc or IId

converted by treatment with an acid in the compounds of formula I with R₁ hydrogen (protonated form); the compounds of the formulas IIa and IIb represent a further subject of the invention;
b) for the preparation of those 3-aryluracil derivatives of the formula I in which R₁ is C₁-C₄-alkyl, C₃- or C₄-alkenyl, C₃- or C₄-alkynyl or C₁-C₄-haloalkyl, a uracil derivative of the formula ic

wherein R₂, R₃, R₄ and R₅ have the meanings given under formula I, and Q 'the group

where R₆, R₇, X₁, R₉ 'and m are as defined under a), in the presence of a corresponding C₁-C₄ alkyl, C₃ or C₄ alkenyl, C₃- or Alkylated C₄-alkynyl or C₁-C₄ haloalkyl group alkylating agent; when Another product may also be the O-alkylation product of the formula Id

be obtained, wherein R₁₁ 'has the meaning given for R₁, with the exception of hydrogen;
c) for the preparation of those 3-aryluracil derivatives of the formula I in which R₄ is chlorine, bromine or iodine, a uracil derivative of the formula Ie or If

wherein R₁, R₂, R₃, R₅, R₆, R₇ and R₁₁ have the meanings given under formula I, Q '' the group

where X₁ is oxygen or S (O) _m ; m is the number 0, 1 or 2; and R₉ '' is C₁-C₅alkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₄alkyl, C₁-C₅-haloalkyl, C₂-C₅- Alkenyl, C₂-C₅ alkynyl, optionally substituted aryl or benzyl, chlorinated, brominated or iodinated;
d) for the preparation of those 3-aryluracil derivatives of the formula Ib (imino ether form)

a 2-halo-3-phenyl-pyrimidin-4-one derivative of formula III  

wherein R₂, R₃, R₄, R₅, R₆ and R₇ have the meanings given under formula I, Q "is the group of formula 4, and Y is bromine or preferably chlorine, base catalysed with an alcohol of the formula R₁₁OH (IV) or with the corresponding alkoxide of the formula R₁₁-O⊖M₂⊕ (V), wherein R₁₁ has the meaning given under formula I, and M₂⊕ is an alkali or alkaline earth metal ion, is reacted; the compounds of the formula III represent a further subject of the invention;
e) for the preparation of those 3-aryluracil derivatives of the formula I in which Q is a group of the formula I in which R₆ is hydrogen and R₇ has the meaning given under formula I, a uracil derivative of the formula VI or VII

wherein R₁, R₂, R₃, R₄, R₅ and R₇ have the meanings given under formula I, and R₁₃ is hydroxy, C₁-C₄-alkoxy or halogen, preferably chlorine, reduced;
f) for the preparation of those 3-aryluraacil derivatives of the formula I in which Q is a group of the formula I in which R₆, R₇ and R₈ have the meaning given for formula I, with the proviso that R₇ is not hydrogen and R₈ is not halogen is a uracil derivative of the formula VIII or IX

wherein R₁, R₂, R₃, R₄, R₅ and R₆ have the meanings given under formula I, and R₁₄ C₁-C₄-alkoxy or halogen, preferably chlorine, with an organometallic compound of the formula Y'-M₂-R₇ (X) or M₂ -R₇ (XI), wherein R₇ is as defined under formula I except hydrogen, and M₂ is a metal cation, preferably lithium or magnesium, and Y 'is an anion, preferably halogen, alkylated;
g) for the preparation of those 3-aryluracil derivatives of the formula I, in which Q is a group of formula I, wherein R₈ is halogen or the group -X₁-R₉ (2), wherein X₁ is oxygen, sulfur, -OSO₂- or -SSO₂ - and R₉ has the meaning given under formula I, with the exception of hydrogen, and if X₁-OSO₂- or -SSO₂-, R₉ is not the group

a uracil derivative of the formula XII

or a reactive salt thereof, wherein R₁, R₂, R₃, R₄, R₅, R₆ and R₇ have the meanings given under formula I; and X₂ is oxygen or sulfur, treated with a halogenating, acylating or alkylating agent;
h) for the preparation of those 3-aryluracil derivatives of the formula I in which Q is the group

wherein X₁ is oxygen or sulfur, and R₉ is the lower  Formula I has indicated meaning, a uracil derivative of the formula XIII

wherein R₁, R₂, R₃, R₄, R₅, R₆ and R₇ have the meanings given under formula I, and R₈ is a leaving group such as halogen, preferably chlorine, bromine or Iodine, or the group -X₁-R₉ (2), wherein X₁ is -OSO₂-, and R₉ is C₁-C₅-alkyl, C₁-C₅-haloalkyl or aryl, with a salt of formula XIV

wherein X₁ 'and X₂ independently oxygen or sulfur; R₁₀ the under Fomel I has the meaning given, and M₃ is an alkali metal cation, preferably lithium, Sodium or potassium cation, or with a salt of formula XV

wherein X₁ 'is oxygen or sulfur; R₉ has the meaning given under formula I; and M₃ is a metal cation, preferably lithium, sodium or potassium cation, reacting with each other;
i) for the preparation of those 3-aryluracil derivatives of the formula I in which Q is a group

wherein s is the number 1 or 2, a uracil derivative of Formula XVI  

wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₉ have the meanings given under formula I with the proviso that R₉ is not hydrogen, reacted with an oxidizing agent;
j) for the preparation of those 3-aryluracil derivatives of the formula I in which R₂ is cyano, a compound of formula I wherein R₂ is halogen, with a metal cyanide of the formula XVII

M₄ (CN) _S (XVII),

wherein M₄ is an alkali metal ion or a metal of the first or second subgroup of Periodic Table; and s is the number 1 or 2, means.

The cyclization according to process variant a) can be carried out expediently be prepared by the compound of formula IIa or IIb in an inert protic organic solvents such as an alcohol, for example, methanol, ethanol or isopropanol; an inert aprotic organic solvent such as an aliphatic or cyclic ethers, for example, 1,2-dimethoxyethane, tetrahydrofuran or dioxane or an aromatic such as benzene or toluene; an inert one aprotic, polar organic solvents, for example dimethylformamide or Dimethyl sulfoxide, such solvents optionally in the two-phase mixture with a hydrocarbon, for example n-hexane or toluene can; or water with a base at temperatures between -78 ° C and the reflux temperature the reaction mixture, preferably at temperatures between 0 ° C and the boiling temperature of the reaction mixture. As bases come preferably Sodium alcoholates, alkali metal hydroxides, especially sodium hydroxide or Potassium hydroxide, alkali metal carbonates, especially sodium carbonate or potassium carbonate or sodium hydride. When using sodium hydride as Base, the solvent is preferably an aliphatic or cyclic ether,  Dimethylformamide or dimethyl sulfoxide, each of these solvents in admixture can be used with toluene.

After completion of the cyclization, the product is in the case of use of the above-mentioned or related bases in the form of the corresponding alkali metal salt in front. This can be isolated and purified in a conventional manner, or you can acidify the mixture to isolate the particular compound of formula I. To this Purpose is preferably a mineral acid, such as hydrochloric acid, or a strong organic acid, such as acetic acid or formic acid.

In the process variant b), the term "alkylated" for the introduction of a C₁-C₄ alkyl, C₃ or C₄ alkenyl, C₃ or C₄ alkynyl or C₁-C₄ haloalkyl group at the unsubstituted nitrogen atom of the uracil nucleus. As the alkylating agent is suitably a C₁-C₄-alkyl halide, C₃- or C₄-alkenyl halide or C₃- or C₄-alkynyl halide, in particular the relevant chloride or bromide, or Sulfonate or a multi-halogenated C₁-C₄ alkane, such as Chlorodifluoromethane, or a mono- or polyhalogenated alkene, such as For example, tetrafluoroethane used.

The alkylation is conveniently carried out in the presence of an inert, protic organic solvent, such as a lower alkanol, for example ethanol, optionally mixed with water, an inert, aprotic organic solvent, such as an aliphatic or cyclic ether, for example 1,2-dimethoxyethane, Tetrahydrofuran or dioxane; a ketone, for example acetone or Butan-2-one; or an inert, aprotic, polar organic solvent, for example Dimethylformamide, dimethyl sulfoxide or acetonitrile, as well as in the presence a base such as sodium hydride, an alkali metal hydroxide, especially sodium or Potassium hydroxide, an alkali metal alcoholate, in particular sodium alcoholate, or a Alkali metal carbonate or bicarbonate, in particular sodium carbonate, potassium carbonate, Sodium bicarbonate or potassium bicarbonate, at temperatures between 0 ° C and the reflux temperature of the reaction mixture, preferably at Room temperature, or in the case of Alkylierun of the N atom in the uracil ring with a C₁-C₄ haloalkyl group, preferably at temperatures between 50 ° C and 100 ° C, carried out. In a preferred embodiment, the uracil derivative of formula Ic first with the base such as sodium hydride, ethanolate or carbonate, in the solvent treated and after a short reaction time with the halide in the same solvent  added. In a further embodiment, the uracil derivative Ic is combined with a dialkyl sulfate in the presence of an alkali metal bicarbonate, in particular Sodium or potassium bicarbonate, in the solvent, for example acetone, at Return temperature reacted. The reaction is usually different used solvent is inert in a relatively short time or ended after a few hours.

The chlorination or bromination according to process variant c) is expediently by means of elemental chlorine or sulfuryl chloride, or elemental bromine or sulfuryl bromide carried out in the presence of an inert organic solvent such as acetic acid or a chlorinated aliphatic hydrocarbon, for example methylene chloride, Chloroform or carbon tetrachloride, and in a temperature range of 0 ° C. to 60 ° C, preferably at room temperature. In addition, the implementation with the help an acid-binding agent, for example, sodium acetate and tertiary Amines, preferably triethylamine, dimethylaniline or pyridine.

In the preparation of the 3-aryluracil derivatives of the formula Ib according to the process variant d) the 2-halopyrimidine-on the formula III is suitably in a Excess of the corresponding alcohol of formula IV as a solvent Temperatures between 0 ° C and 50 ° C, preferably at room temperature in the presence a suitable organic base, for example pyridine reacted. Is this done? Reaction of 2-halopyrimidine-on of the formula III with the corresponding alkoxide of the Formula V, M₂⊕ is preferably an alkali metal ion, for example, sodium or Potassium ion, or an alkaline earth metal ion, for example calcium or magnesium ion. Preferred is the sodium ion.

The reduction according to process variant e) is expediently carried out by means of a metal hydride such as sodium borohydride, lithium borohydride, sodium dihydrido-bis (2-methoxy) ethoxy) -aluminate or diborane, in the presence of an inert, organic Solvent such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or a aromatic solvents such as benzene or toluene, and in one Temperature range from -80 ° C to 60 ° C, preferably at -40 ° C to 25 ° C.

The Grignard reaction according to process variant f) expediently in the presence an inert organic solvent such as diethyl ether, 1,2-dimethoxyethane or tetrahydrofuran and in a temperature range of -80 ° C to + 20 ° C, preferably at -80 ° C to -20 ° C performed.  

The halogenation according to process variant g) is expediently by means of a Hydrogen halide such as hydrogen chloride or hydrogen bromide, in one C₁-C₃-alkylcarboxylic acid or an aqueous solution of the alkylcarboxylic acid, preferably in acetic acid as solvent and in a temperature range of 25 ° C to Boiling temperature of the reaction mixture, preferably in the temperature range between 60 ° C to 100 ° C, performed. The halogenating agent may also be a thionyl halide, for example, thionyl chloride or bromide, being used as the solvent aromatic hydrocarbons, such as benzene or toluene are particularly suitable. you operates in a temperature range of 0 ° C to 30 ° C in the presence of an organic Base, for example triethylamine or pyridine. Phosphorus trihalides are also suitable For this purpose, for example, phosphorus tribromide in diethyl ether at temperatures from -25 ° C to + 25 ° C in the presence of pyridine as the base are used. The starting compound is conveniently a uracil derivative of the formula XII used in which X₂ is an oxygen atom.

Suitable acylating agents in process variant g) are expediently reactive Derivatives of carboxylic acids such as acid halides, especially acid chlorides, Acid anhydrides, N-acylimidazolides or O-Acylisoureas used. in the Case of using carboxylic acid halides, sulfonic acid halides or Carbonic acid ester halides or anhydrides of the corresponding acids, arrives inert, organic, aprotic solvent such as aliphatic or cyclic ethers, for example, 1,2-dimethoxyethane, tetrahydrofuran or dioxane, as well as polar solvents, For example, dimethyl sulfoxide or acetonitrile, preferably in the presence of a organic base, such as triethylamine or pyridine at temperatures between -20 ° C and the reflux temperature of the reaction mixture, preferably in Temperature range from -20 ° C to 50 ° C, for use. If the starting product of Formula XII as a reactive derivative, d. H. is present as a salt, the presence of a organic base not required.

As alkylating agent in process variant g) is suitably a corresponding halide, in particular the relevant chloride, bromide, or sulfate, or a multi-halogenated C₁-C₄ alkane used.

The alkylation is conveniently carried out in the presence of an inert, protic organic solvent such as a C₁-C₃ alcohol, for example, ethanol, optionally  in a mixture with water; an inert, aprotic organic solvent, such as an aliphatic or cyclic ether, for example 1,2-dimethoxyethane, Tetrahydrofuran or dioxane; or an inert, aprotic, polar organic Solvent, for example dimethylformamide, dimethyl sulfoxide or acetonitrile, as well as in the presence of a base, such as sodium hydride, of an alkali metal hydroxide, in particular Sodium or potassium hydroxide, an alkali metal alcoholate Sodium alcoholate, or an alkali metal carbonate or bicarbonate, in particular Sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, at temperatures between 0 ° C and the reflux temperature of Reaction mixture, preferably at reflux temperature performed. In a In a preferred embodiment, the uracil derivative of formula XII is first reacted with the Base, such as sodium hydride, sodium ethoxide or sodium carbonate, in the solvent treated and after a short reaction time with the halide or sulfate in the same Solvent added. For the reaction is suitably a reactive salt of Uracilderivates of formula XII used.

In the preparation of the compounds of the formula I according to process variant h) is in reactive derivative of the formula XIII the leaving group R₈ by means of a salt of the formula Substituted XIV or XV. Appropriately, this reaction takes place in one protic, organic solvents, such as one corresponding to the radical R₉ aliphatic alcohol. Also suitable are aprotic solvents, such as aliphatic ketones, for example acetone or 2-butanone, and aliphatic or cyclic ethers, for example, 1,2-dimethoxyethane, tetrahydrofuran or dioxane and polar solvents, such as dimethylformamide, dimethyl sulfoxide, 1,3-dimethyl 3,4,5,6-tetrahydro-2- (1, H) -pyrimidone, N-methylpyrrolidone or acetonitrile. you works at temperatures between -20 ° C and the reflux temperature of the reaction mixture, preferably in the temperature range from 25 ° C to 100 ° C.

The oxidation according to process variant i) is expediently by means of aliphatic or aromatic peracids, for example peracetic acid or 3-chloroperbenzoic acid, or inorganic oxidizing agent, such as sodium metaperiodate, sodium perborate, Potassium monopersulfate or hydrogen peroxide in an inert, protic organic solvents, such as aliphatic carboxylic acids, preferably in acetic acid or aliphatic alcohols, especially in methanol. to Organic, aprotic solvents, for example aliphatic ones, are also used Hydrocarbons or halogenated hydrocarbons, such as  n-heptane, dichloromethane, or 1,2-dichloroethane, or aliphatic ketones, preferably Acetone, wherein also aqueous mixtures of said solvents come into question. Work is carried out at temperatures between -70 ° C and 100 ° C, preferably in the temperature range from -15 ° C to 35 ° C.

In the preparation of 3-aryluracil derivatives of the formula I, wherein R₂ is a cyano group is, according to the process variant j) is an aromatic halogen substituent (R₂ = Halogen) replaced by a cyano group by means of a metal cyanide of Formula XVII. The latter is especially a transition metal cyanide, preferably Copper (I) cyanide. The exchange reaction is conveniently carried out in the presence of a aprotic, polar solvent, such as alkyl nitrile, for example, aceto, propio or Butyronitrile, or in the presence of an alkylurea, for example tetramethylurea, or a dialkylamide, for example dimethylformamide, or a Dialkylsulfoxids, for example dimethyl sulfoxide or in N-methyl-2-pyrrolidone, 1,3-dimethyl-imidazolidin-2-one, 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone, Hexamethylphosphorsäuretriamid at Temperautren between + 80 ° C and + 200 ° C, preferably between + 150 ° C to + 200 ° C.

The salts of the compounds of the formula I thus obtained, in which R₁ is hydrogen, can be prepared in a conventional manner, such as by dissolution the compounds of the formula I in the presence of an inorganic or organic base. Salt formation usually takes place in an inert, short time at room temperature. In a Embodiment, the sodium salt by dissolving the uracil derivative I in aqueous Sodium hydroxide solution prepared at room temperature, with equivalent amounts of Uracilderivats and sodium hydroxide are used. The solid salt can then by precipitation with a suitable inert solvent or by evaporation of the Be isolated solvent. Another embodiment is a aqueous solution of an alkali metal salt of uracil derivative I in an aqueous solution a salt having a metal cation other than an alkali metal cation, wherein the second metal salt of the uracil derivative is prepared. This embodiment generally serves for the production of uracil metal salts, which in Water are insoluble.

The resulting compounds of formula I and their salts can be known per se Methods are isolated and purified. Furthermore, the person skilled in the art is familiar in which order certain reactions under the process variants a) to j) expedient  To be able to carry out possible, undesirable competing reactions avoid.

If no specific synthesis for the isolation of pure isomers is carried out, the Product obtained as a mixture of two or more isomers. The isomers can after be separated by methods known per se. If desired, for example pure optically active Iosmere also by synthesis of corresponding optically active Starting materials are produced.

The starting compounds of the formulas IIa and IIb are new and can be prepared in analogy to known methods, for. For example, EP-A 02 60 621 are prepared, for. B. according to the following reaction Schemes 1 and 2 (methods aa), bb), cc), dd), ee), ff) and gg)).

Reaction Scheme 1 Method aa) Method bb) Method cc) Method dd) Reaction scheme 2 Method ee) Method ff) Method gg)

In Reaction Schemes 1 and 2, R₂, R₃, R₄ ', R₅, R₅', R₁₂ and Q 'have the meanings defined above; R₄ '' is hydrogen or C₁-C₄ alkyl; or R₄ '' and R₅ 'taken together - (CH₂) _n -, where n is the number 3 or 4; R₅ is C₁-C₄alkyl; and R₁₅ is hydrogen or C₁-C₃ alkyl.

The reaction according to the method aa) in Reaction Scheme 1 is expediently carried out by reacting the compounds of the formula XVIII 'and XIX in an anhydrous solvent and react with each other acid catalysed at elevated temperature. When Solvents come especially with water azeotroping organic solvents, for example, benzene, toluene and xylenes; or halogenated hydrocarbons, for example, methylene chloride, chloroform, carbon tetrachloride or chlorobenzene; or aliphatic or cyclic ethers, for example 1,2-dimethoxyethane, tetrahydrofuran or dioxane in question; acid catalysts are, in particular, strong mineral acids, for example, sulfuric acid or hydrochloric acid; organic acids, for example p-toluenesulfonic acid; Phosphorus-containing acids, for example orthophosphoric acid or polyphosphoric acid; or acidic cation exchanger, for example "Amberlyst 15" (Fluka), in question. The reaction temperatures are in the range of about 70 ° C to 120 ° C, preferably at the reflux temperature of the reaction mixture. Under these Reaction conditions, a rapid removal of the formed in the reaction Achieved water.

The reaction according to the method bb) is conveniently carried out in the presence of a anhydrous, aprotic, organic solvent, for example an aliphatic or cyclic ether, preferably diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane; an aliphatic or aromatic hydrocarbon, for example n-hexane, benzene, toluene or xylene; or a halogenated aliphatic hydrocarbon, for example, methylene chloride, carbon tetrachloride or 1,2-dichloroethane, and optionally in the presence of a base, in particular an organic, tertiary base, for example triethylamine or pyridine, the latter both as Solvent may serve as a base, or a metal hydride, for example Sodium or potassium hydride. The reaction temperatures are in the range of about -80 ° C to + 50 ° C, preferably between -30 ° C and room temperature.

The reaction according to the method cc) is carried out analogously to the method bb) with the difference however, that the reaction temperatures preferably in the range of about -80 ° C to 150 ° C, in particular between 0 ° C and 130 ° C.  

The reaction according to the method dd) is advantageously carried out in an inert, with Water-miscible, organic solvents, for example in an aliphatic or cyclic ethers, preferably 1,2-dimethoxyethane, tetrahydrofuran or dioxane, or in a lower alkanol, preferably ethanol, at temperatures between 50 ° C and 100 ° C, preferably at the reflux temperature of the reaction mixture, or in an aromatic solvent, for example benzene, toluene or in a xylene, in Presence of an acid catalyst, for example hydrochloric acid or p-toluenesulfonic acid, at temperatures between 50 ° C and 100 ° C, preferably between 60 ° C to 80 ° C.

The reaction of the aniline derivative of the formula XXIII with the diketene of the formula XXII according to the method ee) in Reaction Scheme 2 is expediently carried out in an anhydrous, inert, aprotic solvents, for example a halogenated hydrocarbon, preferably methylene chloride, chloroform, carbon tetrachloride or Chlorobenzene; or an aromatic hydrocarbon, for example benzene, toluene or a xylene; or an aliphatic or cyclic ether, for example diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane. The reaction proceeds base catalysis, for example in the presence of 4-pyrrolidino-pyridine, 4-dimethylaminopyridine, 1,4-diazabicyclo [2.2.2] octane, 1,5-diazabicyclo [4,3,0] non-5-ene, 1,8-diazabicyclo- [5,4,0] undec-7-ene or diethylamine. Since the reaction is exothermic, one generally works in a temperature range of -10 ° C to + 50 ° C, preferably at room temperature.

The reaction of the compounds of the formulas XXV and XXIII according to the method ff) is suitably added in an anhydrous, inert, aprotic solvent Temperatures between 70 ° C to 140 ° C, preferably between 100 ° C to 120 ° C performed. Particularly suitable solvents are aromatics, for example benzene, Toluene or xylenes; halogenated hydrocarbons, for example carbon tetrachloride, Trichloroethane, tetrachloroethane or chlorobenzene; or aliphatic or cyclic Ethers, for example dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane.

In the implementation of the method gg) is an aminolysis, which expediently in an anhydrous solvent or without solvent [see for example J. Soc. Dyces Col. 42, 81 (1926); Ber. 64, 970 (1931); and J. Am. Chem. Soc. 70, 2402 (1948)] at elevated temperature. As a solvent in particular inert, aprotic solvents, such as optionally halogenated aromatics, for example Toluene, xylenes or chlorobenzenes, in question. You generally work in  a temperature range between 130 ° C to 160 ° C. If necessary, also in the presence a basic catalyst worked, for example, a higher boiling Amines [see, for example, Helv. Chim. Acta 11, 779 (1928); and US Patent No. 24 16 738] or pyridine.

The subsequent reaction of the compounds of formula XXIV thus prepared, XXVI resp. XXVII with the carbamic acid ester of formula XXVIII is conveniently carried out in an anhydrous solvent and in the presence of an acidic Catalyst at elevated temperature. As solvents come in particular with Water azeotropes forming organic solvents, for example aromatic Hydrocarbons, preferably benzene, toluene or xylenes; or halogenated hydrocarbons, for example, carbon tetrachloride or chlorobenzene, and as acidic Catalysts preferably strong mineral acids, for example sulfuric acid; organic acids, for example p-toluenesulfonic acid; Phosphorus-containing acids, for example Orthophosphoric acid or polyphosphoric acid; or acidic cation exchanger, For example, "Amberlyst 15" (Fluka), into consideration. The temperatures used are in the range of 70 ° C to 150 ° C, preferably at the reflux temperature of Reaction mixture. Under these reaction conditions, the desired rapid Removal of the water formed in the reaction achieved.

The preparation of the starting compounds of the formula VI and VII, and the corresponding Enol ethers are known in part from EP-A 01 95 346 and EP-A 02 60 621. Those starting materials VI and VIII and enol ethers, their preparation is not described, can be prepared analogously to the known starting materials become.

The starting compounds (benzaldehydes and phenones) of the formula IX can by Oxidation can be made from the corresponding benzyl alcohol derivatives.

In the oxidation, a benzyl alcohol of the formula I in which R₈ is the expediently Group -X₁-R₉ (2), wherein R₆ or / and R₇ and R₉ are hydrogen, with a suitable oxidizing agents, such as pyridinium dichromate, pyridinium chlorochromate, Potassium permanganate, ruthenium tetroxide or manganese dioxide in an inert, organic solvents, such as in chlorinated hydrocarbons, such as Carbon tetrachloride or dichloromethane or in an aliphatic nitrile such as Acetonitrile, oxidized. As further solvents can also acetic acid or  Mineral acids, such as sulfuric acid are used. The applied Reaction temperatures are between -20 ° C and + 50 ° C, preferably between 0 ° C. and + 30 ° C. In a preferred embodiment, the benzyl alcohol of the formula I oxidized with pyridinium chlorochromate in dichloromethane.

The starting materials of the formula III used in process variant f) can by halogenation of the corresponding uracil derivatives of the above-indicated formula Ic getting produced. For this halogenation is used as halogenating agent in particular Thionyl chloride, phosphorus pentachloride or phosphorus oxychloride or phosphorus pentabromide or phosphoryl bromide. Optionally, a mixture of phosphorus pentachloride and phosphorus oxychloride and phosphorus pentabromide and phosphoryl bromide, respectively used, with an excess of phosphorus oxychloride or phosphoryl bromide can serve as a solvent. The chlorination or bromination can also in the presence of an inert solvent, in particular an aprotic, organic solvent, for example an aliphatic or aromatic Hydrocarbon, preferably n-hexane, benzene, toluene or a xylene; one halogenated, aliphatic hydrocarbon, preferably methylene chloride, Chloroform or 1,2-dichloroethane; a halogenated aromatic hydrocarbon, preferably chlorobenzene, or a tertiary amine, preferably N, N-dimethylaniline. When using thionyl chloride as Halogenating agent advantageously becomes a catalytic amount of dimethylformamide added. The reaction temperatures are generally between 0 ° C and the Reflux temperature of the reaction mixture, preferably between 80 ° C and 120 ° C.

When serving as starting materials in process variants b), c), g), h) and i) Uracilderivaten of formula Ic, Ie, XII, XIII and XVI and their enol ethers are subgroups of compounds of formula I. The remaining in the process variants a) to j), as well as in the reaction Schemes 1 and 2 used starting compounds or reagents are either known or can be known per se Methods are produced.

It has now been found that the compounds of the formula I (im hereinafter also referred to as "active ingredients") and their enol ethers or salts valuable Active substances having herbicidal properties are and are useful for controlling weeds, including grass weeds, including Agropyron repens, Alopecurus myosuroides, Avena fatua, Bromus inermis, Echinochloa crus-galli, Poa annua, Sorghum  Halepense, Abutilon theophrasti, Amaranthus retroflexus, Cassia obtusifolia, Chenopodium album, Galium aparine, Matricaria chamomilla, Sinapis arvensis and Stellaria media, in various crops, so u. a. Crops of rice, rice, wheat, maize, soya, oilseed rape and cotton. In addition are the compounds include both pre-emergence and post-emergence herbicides. For some Representatives of the compounds of the formula I have shown good selectivity, For example, in the control of weeds in soybean and cotton crops.

In practice, a concentration of 1 g to 3 kg of the compound usually suffices of the formula I per ha, preferably from 10 g to 1 kg / ha, of the desired herbicidal Effect to achieve. To the desired herbicidal effect with optimal crop compatibility is the range of 10 to 100 g / ha in the pre-emergence treatment and from 100 to 1000 g / ha in postemergence treatment in particular Cheap.

Furthermore, the active substances of the formula I can not only be used as weed control agents, but also as a desiccant for harvest relief in crops such as cotton, Potatoes and rape are used.

The weed control agents of the present invention contain at least an effective amount a compound of formula I, or an enol ether or salt thereof, and in all rule also formulation aids. Conveniently, they contain at least one formulation adjuvant from each of the following groups:

- solid carriers;
- solvent or dispersant;
- Surfactants (wetting agents and emulsifiers);
- Dispersant (without surfactant effect); and
- stabilizers.

The pesticidal preparations generally contain, in addition to the active compounds of the formula I 1 to 99% of a formulation auxiliary from the group

- solid carriers;
- solvent or dispersant;
- Dispersant (without surfactant effect); and
- stabilizers; and 0 to 25%, especially 0.1 to 25% of a surfactant (wetting agents and emulsifiers).

Using such and other adjuvants, the compounds of the Formula I, d. H. the herbicidal active ingredients, in the usual formulations, such as dusts, Powders, granules, solutions, emulsions, suspensions, emulsifiable concentrates, Pastes and the like are transferred.

The compounds of the formula I and their enol ethers are generally water-insoluble, the salts, however, in particular the alkali metal salts, in general water-soluble, and may according to the water-insoluble or water-soluble Compounds conventional methods using the known formulation adjuvants be made up. The preparation of the agent can in a conventional manner be carried out, for example by mixing the respective active substance with solid carriers, by dissolving or suspending in appropriate solution or Dispersing agents, optionally using surfactants as wetting agents or Emulsifiers and / or dispersants, or by dilution already prepared emulsifiable concentrates with solvents or dispersants.

Suitable solid carriers are essentially:

- Natural minerals, such as chalk, dolomite, limestone, clays and silica or their salts, for example diatomaceous earth, kaolin, bentonite, talc, attapulgite or montmorillonite;
- synthetic minerals, such as fumed silica, alumina or silicates;
- organic substances such as cellulose, starch, ureas or synthetic resins; or
- Fertilizers, such as phosphates or nitrates. Such carriers can be present, for example, as powders or as granules.

Suitable solvents or dispersants are essentially: aromatics, such as Benzene, toluene, xylenes and alkylnaphthalenes; -chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride; aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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; or strongly polar solvents or dispersants, such as dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide (such solvents preferably having flash points of at least 30 ° C and boiling points of at least 50 ° C) or  Water. Next come as solvents or dispersants and so-called ver liquid gaseous diluents or carriers which are products of Room temperature and under atmospheric pressure are gaseous, in question. Examples of such In particular, products include aerosol propellants, such as halogenated hydrocarbons For example, dichlorodifluoromethane. Is the weed control according to the invention medium in the form of a pressurized gas, it is expediently in addition to Propellant used a solvent.

The surfactants (wetting agents and emulsifiers) may be nonionic compounds, such as: - Condensation products of fatty acids, fatty alcohols or fatty-substituted phenols with ethylene oxide; Fatty acid esters and ethers of sugars or polyhydric alcohols; - the products obtained from sugars or polyhydric alcohols by condensation with Ethylene oxide are obtained; Block polymers of ethylene oxide and propylene oxide; or - Alkyldimethylamine.

The surfactants may also be anionic compounds, such as: soaps; - fat sulfate ester, for example, dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulfate; - Alkyl sulfonates, aryl sulfonates or fatty aromatic sulfonates, such as alkylbenzenesulfonates, for example, calcium dodecylbenzenesulfonates; or - more complex fatty sulfonates, for example the amide condensation products of oleic acid and N-methyl taurine or the sodium sulfonate of dioctyl succinate.

Finally, the surfactants may be cationic compounds, such as alkyl dimethylbenzene cylammonium chlorides, dialkyldimethylammonium chlorides, alkyltrimethylammonium chloride or ethoxylated ammonium chlorides.

Suitable dispersants (without surfactant action) are essentially: lignin, Sodium and ammonium salts of lignosulfonic acids, sodium salts of maleic acid anhydride-diisobutylene copolymers, sodium and ammonium salts of sulfonated Polycondensation products of naphthalene and formaldehyde, or sulfite liquors.

As a dispersant, which in particular as thickening or Antiabsetzmittel For example, methylcellulose, carboxymethylcellulose, hydroxy ethylcellulose, polyvinyl alcohol, alignates, caseinates and blood albumin.

Examples of suitable stabilizers are: Acid-binding agents, for example  Epichlorohydrin, phenyl glycidyl ether or soya epoxides; - Antioxidants, for example Gallic acid ester or butylhydroxytoluene; UV absorbers, for example substituted ones Benzophenones, diphenylacrylonitrile acid esters or cinnamic acid esters; or - deactivators, for example, salts of ethylenediaminetetraacetic acid and polyglycols.

The weed control agents according to the invention can be used in addition to the inventions active substances according to the invention synergists and other active ingredients, such as Insecticides, acaricides, nematocides, molluscicides, bactericides, fungicides, herbicides, Plant growth regulators, fertilizers and trace element mediators included. Such combination agents are suitable for widening the activity spectrum.

The weed control agents according to the invention generally contain between 0.001 and 95 weight percent, preferably between 0.5 and 75 weight percent, one or several compounds of the formula I according to the invention as active ingredient (e). you For example, they may be in a form suitable for storage and storage Transport is suitable. In such formulations, for example emulsifiable concentrates, the drug concentration is usually in the higher range, preferably between 1 and 50 weight percent, especially between 5 and 30 weight percent. These Formulations can then, for example, with the same or different inert Substances diluted to the active substance concentration, which are suitable for practical use Use is suitable, so preferably about 0.001 to 10 weight percent, especially about 0.005 to 5 weight percent. However, the drug concentrations may also be smaller or bigger.

As mentioned, the preparation of the weed control compositions according to the invention in be carried out in a known manner.

For the preparation of powdered preparations, the active ingredient, d. H. at least one inventive compound of formula I mixed with a solid carrier be, for example, by grinding together. Or you can the solid carrier impregnated with a solution or suspension of the active substance and then the solution or dispersing agent by evaporation, heating or suction under reduced Remove pressure. By adding surfactants or dispersants can be such make powdery means easily wettable with water, so that they are in aqueous Suspensions that are suitable, for example, as a spray can be converted.  

The active ingredient of the formula I can also with a surfactant and a solid carrier for Forming a wettable powder which is dispersible in water, are mixed, or he can use a solid, pre-granulated carrier to form a granule shaped product are mixed.

If desired, the active compound of the formula I can be mixed in a water-immiscible Solvent, such as a high boiling hydrocarbon, dissolved become. This contains expediently dissolved emulsifier, so that the solution at self-emulsifying to its addition to water. On the other hand, the active ingredient with a Emulsifier mixed and then the mixture with water to the desired concentration be diluted. In addition, the active ingredient can be dissolved in a solvent and then mixed with an emulsifier. Such a mixture can also with Water to be diluted to the desired concentration. In this way you get emulsifiable concentrates or ready-to-use emulsions.

The use according to the invention of the weed control compositions described can according to usual application methods, such as spraying, spraying, dusting, pouring or Sprinkle, done.

The following examples serve to illustrate the invention.

A. Preparation of the compounds of the formula I according to the invention example 1 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] -benzyl alcohol

To a solution of 114.0 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro Methyl-1 (2H) -pyrimidinyl] benzoyl chloride in 1.2 l of tetrahydrofuran is stirred at -80 ° C in a nitrogen atmosphere for 1.5 hours 98.8 g of a 70% solution of sodium dihydro-bis (2-methoxyethoxy) -aluminate in toluene containing 480 ml absolute toluene is diluted, added dropwise. Thereafter, the reaction temperature on Increased -30 ° C and for 15 minutes, a solution of 180 ml of concentrated hydrochloric acid and 300 ml of water are added dropwise, the temperature rises to + 10 ° C. The two phase mixture is separated, the aqueous phase with 250 ml of ethyl acetate extracted and the combined organic phases with an aqueous sodium chloride solution washed. The organic solution is poured over anhydrous sodium sulfate dried and evaporated under reduced pressure. The resulting solid residue is dissolved in  Slurried 100 ml of ethyl acetate at 50 ° C and then cooled to 20 ° C and with 200 ml of diethyl ether. The crystals are filtered off with suction, with diethyl ether washed and dried; Mp .: 192-194 ° C.

Example 2 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] -4-fluorobenzyl alcohol

A solution of 3.2 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H) -pyrimidinyl] -4-fluorobenzoyl chloride in 50 ml of absolute tetrahydrofuran is added 0.17 g of sodium borohydride are added at 0 ° C. with stirring and then at 60 ° C. for 36 hours touched. The reaction mixture is concentrated under reduced pressure and the residue taken up in 150 ml of ethyl acetate, first with 200 ml of 1N hydrochloric acid and then washed twice with 200 ml of water. The organic phase becomes dried over sodium sulfate and concentrated on Rotovap. The resulting residue is via silica gel with ethyl acetate / n-hexane 1/1 as the eluent chromatographically purified and recrystallized from diethyl ether / n-hexane; Mp .: 113-116 ° C.

Example 3 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] -benzyl bromide

To a solution of 25.0 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H) -pyrimidinyl] -benzyl alcohol in 250 ml of acetic acid is added under stirring to 100 ml of 48% Hydrobromic acid added and this solution was stirred at 75 ° C for 21 hours. to closing the reaction mixture is concentrated under reduced pressure, the solid Residue dissolved in 1 l of ethyl acetate and this solution twice with 500 ml Water, then with 500 ml of 5% sodium bicarbonate solution and finally with Washed 500 ml of water. The neutral, organic phase is dried over sodium sulfate, concentrated under reduced pressure and from ethyl acetate / n-hexane recrystallized; Mp .: 169-171 ° C.

Example 4 Methanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-tri fluoromethyl-1 (2H) -pyrimidinyl] benzyl) ester

To a solution of 51.1 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro Methyl-1 (2H) -pyrimidinyl] -benzyl alcohol is added to 20.6 g of methanesulfonyl chloride in 750 ml absolute tetrahydrofuran at 0 ° C with stirring for 1 hour, a solution added dropwise of 18.2 g of triethylamine in 200 ml of tetrahydrofuran; the reaction temperature rises to + 10 ° C. The mixture is then stirred for 30 minutes, the insoluble fractions separated and the clear solution concentrated under reduced pressure. The solid residue  is recrystallized from ethyl acetate / n-hexane; Mp .: 139-140 ° C.

Example 5 2-propanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-tri- fluoromethyl-1 (2H) -pyrimidinyl] benzyl) ester

Analogously to Example 4 is obtained by esterification of 2-chloro-5- [3,6-dihydro- 2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl alcohol with 2-propane sulfonyl chloride, the 2-propanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-tri- fluoromethyl-1 (2H) -pyrimidinyl] -benzyl) ester, 1 H-NMR. (CDCl₃, 200 MHz): 7.56 ppm (d, 1H), 7.39 ppm (d, 1H), 7.21 ppm (q, 1H), 6.38 ppm (s, 1H), 5.35 ppm (s, 2H), 3.56 ppm (d, 3H), 3.28 ppm (m, 1H), 1.42 ppm (d, 6H).

Example 6 Isobutyric (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-tri fluoromethyl-1 (2H) -pyrimidinyl] benzyl) ester

Analogously to Example 4 is obtained by esterification of 2-chloro-5- [3,6-dihydro- 2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl alcohol with isobutane acid chloride and pyridine as the base isobutyrate (2-chloro-5- [3,6-dihydro-2,6- dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] benzyl) ester; Mp: 117-118 ° C.

Example 7 (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] benzyl) -isopropylether

0.17% of a 55% sodium hydride dispersion is mixed with 20 ml of absolute isopropyl alcohol added and stirred until the evolution of hydrogen. Subsequently 1.51 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyr-imidinyl] - Benzylbromid added and stirred for 2 hours at 50 ° C. The reaction mixture is neutralized with acetic acid and concentrated under reduced pressure. The residue is dissolved in 50 ml of ethyl acetate, twice with 50 ml of water washed, the organic phase dried over sodium sulfate and under reduced Evaporated pressure. The residue is purified on a silica gel with Methylene chloride as the eluent; Mp .: 94-96 ° C.

Analogously to Example 7, the compounds of the formula Ig listed in Table 1 are prepared.  

Table 1

Compounds of the formula Ig

Example 11 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] benzyl) -isopropylsulfon

To a solution of 1.4 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro methyl-1 (2H) -pyrimidinyl] -benzyl-isopropylthioether in 50 ml of methylene chloride with stirring at 0 ° C 1.84 g of m-chloroperbenzoic acid added; the temperature is rising at 10 ° C. This reaction mixture is allowed to stand at room temperature for 20 hours stirred, twice with dilute sodium bicarbonate solution and then with Washed water and dried over sodium sulfate. The organic phase is absorbed Concentrated reduced pressure and the residue from ethyl acetate / diethyl ether recrystallized; Mp .: 147-150 ° C.

B. Preparation of the compounds of the formula I according to the invention from known starting compounds Example 12 1- (2-chloro-5-nitrophenyl) -ethanol

0.9 g of lithium borohydride are dissolved in 40 ml of tetrahydrofuran and cooled to 0 ° C. A solution of 8.0 g of 2-chloro-5-nitro-aceto is added to this solution for 40 minutes  Phenone in 40 ml of tetrahydrofuran was added dropwise. The reaction mixture is during Stirred for 3 hours at 0 ° C. Now carefully 90 ml of 2N hydrochloric acid are added dropwise. After the end of the addition, 100 ml of water are added and the reaction mixture is added twice extracted with 300 ml of ethyl acetate. The organic phase is washed twice 200 ml of 2N hydrochloric acid and twice with 100 ml of saturated saline nachge wash, dried over anhydrous magnesium sulfate and evaporated. The obtained Residue is recrystallized from diisopropyl ether / n-hexane; Mp: 85-88 ° C.

Analogously to Example 12, the compounds listed in Table 2 are the Formula IV produced.

Table 2

Compounds of formula IV

Example 17 1- (5-amino-2-chlorophenyl) ethanol

39 g of iron powder in 50 ml of ethanol, 21 ml of water and 2.5 ml conc. Hydrochloric acid under Stirring slurried and heated to 60 ° C. To this mixture, a solution of 35.8 g of 1- (2-chloro-5-nitrophenyl) ethanol in 90 ml of ethanol are added dropwise during 90 minutes, wherein the reaction temperature rises to 80 ° C. It will be in during 2 hours Reflux temperature heated. After cooling, the reaction mixture with 600 ml Diluted with water, and adjusted to about 9 with 2N potassium carbonate solution, the pH. It is filtered with suction through Celite and the filter material washed with 400 ml of ethyl acetate. The filtrate is transferred to a separatory funnel and shaken. After Phase separation, the aqueous phase is discarded and the organic phase with 200 ml washed up with saturated saline solution. It is over anhydrous sodium sulfate dried and concentrated. The residue is extracted from ethyl acetate / n-hexane recrystallized; Mp: 92-94 ° C.

Analogously to Example 17, the compounds listed in Table 3 are the Formula V produced.  

Table 3

Compounds of the formula V

Example 22 3- (1-hydroxyethyl) -4-chlorcarbanilsäureethylester

35.5 g of 1- (5-amino-2-chloro-phenyl) -ethanol are initially charged in 120 ml of pyridine at 0 ° C. For this purpose, 28 g of ethyl chloroformate are added dropwise, and the mixture during Stirred for 2 hours at room temperature. The reaction mixture is reduced to 600 g crushed ice, and extracted twice each time 300 ml of ethyl acetate. The Organic phases are washed four times with 300 ml of 2N hydrochloric acid and twice with each 300 ml of saturated sodium chloride solution, washed over anhydrous magnesium dried sulfate and concentrated. The residue is extracted from ethyl acetate / n-hexane recrystallized; Mp .: 146-148 ° C.

Analogously to Example 22, the compounds listed in Table 4 are the Formula VI produced.  

Table 4

Compounds of the formula VI

Example 27 1- (2-chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) - pyrimidinyl] phenyl) ethanol

2.1 g of 60-65% sodium hydride suspension in white oil are dissolved in 50 ml of dimethylformamide submitted. For this purpose, 7.5 g of 3-amino-4,4,4-trifluorcrotonsäureethylester in 20 ml Dimethylformamide added dropwise during 40 minutes. After completion of hydrogen evolution 10.0 g of ethyl 3- (1-hydroxyethyl) -4-chloro-carbanylate in 40 ml of dimethyl formamide added dropwise during 30 minutes. The reaction mixture is for 3 hours heated to 150 ° C, wherein the ethanol formed during the reaction continuously from is distilled. The reaction mixture is added to 200 g of ice and 200 ml of 2N hydrochloric acid, and then extracted twice with 300 ml of ethyl acetate. The organic ones Phases are twice with 200 ml of water and once with 200 ml of saturated Washed sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated. The residue is flashchroma over silica gel with ethyl acetate tographed, and the product obtained from acetone / n-hexane recrystallized; Mp .: 190-194 ° C.

Analogously to Example 27, the compounds listed in Table 5 are the Formula Ih made.  

Table 5

Compounds of the formula Ih

Example 34 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro methyl-1 (2H) -pyrimidinyl] -benzyl alcohol

3.2 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl] benzyl alcohol, 1.3 g of dimethyl sulfate and 1.4 g of potassium carbonate in 60 ml of acetone during Heated to reflux for 3 hours. The reaction mixture is evaporated, and the residue mixed with 150 ml of water. It is extracted twice with 150 ml of ethyl acetate each time obtained organic phases twice with 150 ml of saturated sodium chloride solution washed, dried over anhydrous sodium sulfate and evaporated, and the residue is recrystallized from ethyl acetate / n-hexane; Mp .: 193-195 ° C.

Analogously to Example 34, the compounds listed in Table 6 are the Obtained formula II.  

Table 6

Compounds of the formula Ii

Example 41 1- (2-chloro-5- [2-methoxy-6-oxo-4-trifluoromethyl-1 (6H) - pyrimidinyl] phenyl) ethanol

8.4 g of 1- (2-chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidin-yl] -phenyl) - ethanol, 3.7 g of dimethyl sulfate and 3.5 g of potassium carbonate in 140 ml of acetone refluxed for 5 hours. The reaction mixture is added to half of the Volume evaporated and treated with 250 ml of 1N hydrochloric acid. It will be twice with each Extracted 300 ml of ethyl acetate, and the combined organic phases twice washed with 200 ml of saturated sodium chloride solution and over anhydrous Dried magnesium sulfate and evaporated. The thin-layer chromatogram (Run ethyl acetate / n-hexane 1/2) shows two products in UV light (254 nm), the by flash chromatography and ethyl acetate / n-hexane 1/2 as the eluent be separated. The first product is 1- (2-chloro-5- [2-methoxy-6-oxo-4-trifluoro methyl-1 (6H) -pyrimidinyl] -phenyl) -ethanol as a yellow oil; H-NMR. (D₆-DMSO, 200 MHz): 7.59 ppm (d, 1H), 7.54 ppm (d, 1H), 7.30 ppm (dxd, 1H), 6.72 ppm (s, 1H), 5.03 ppm (q, 1H), 3.89 ppm (s, 3H).

The second product is 1- (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro methyl-1 (2H) -pyrimidinyl] -phenyl) -ethanol eluted from ethyl acetate / n-hexane recrystallized, crystals with mp.: 156-159 ° C yields.

Analogously to Example 41, the compounds listed in Table 7 are the Formula Ij produced.  

Table 7

Compounds of the formula Ij

Example 47 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-allyl-4-trifluoromethyl- 1 (2H) -pyrimidinyl] -benzyl alcohol

0.5 g of sodium hydride (50% dispersion in white oil) is dissolved in 20 ml of N, N-dimethylformamide submitted at room temperature and within 15 minutes, a solution of 3.2 g 2-Chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl alcohol in 30 ml of N, N-dimethylformamide was added dropwise and stirred for 2 hours. Subsequently 2.4 g of allyl bromide are added and the reaction mixture stirred for a further 16 hours. The reaction is stopped by pouring onto 200 ml of ice water and the crude product by extraction with ethyl acetate, and washing the organic phase with saturated sodium chloride solution and drying over sodium sulfate. The Purification is carried out over a silica gel with ethyl acetate / n-hexane as Eluent and then by recrystallization from diethyl ester / n-hexane; Mp: 125-126 ° C.

Example 48 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-propargyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] -benzyl alcohol

is obtained analogously to Example 47 by using proparyl bromide; Mp: 153-154 ° C.

Example 49 1- (2-chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) - pyrimidinyl] phenyl) propanol

0.22 g of lithium borohydride is added in 10 ml of tetrahydrofuran under a nitrogen atmosphere 0 ° C submitted. Within 15 minutes, a solution of 3.50 g of 2-chloro-5- [3,6- dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl] -propiophenone in 20 ml tetra  hydrofuran was added dropwise and the mixture stirred for 90 minutes at 0 ° C. Subsequently is added dropwise within 15 minutes 25 ml of 2N hydrochloric acid and twice with each Extracted 100 ml of ethyl acetate. The combined organic phases become twice with 70 ml of 2N hydrochloric acid and twice with 70 ml of saturated sodium washed chloride solution, dried over sodium sulfate and evaporated. The obtained Residue is recrystallized from ethyl acetate / n-hexane; Mp: 199-201 ° C.

Example 50 1- (2-chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) - pyrimidinyl] phenyl) -1-methylpropanol

4.0 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl] propio phenone is placed in 15 ml of tetrahydrofuran at -10 ° C. This will be done within 8.5 g of 22% methylmagnesium chloride solution in tetrahydrofuran was added dropwise for 15 minutes and stirred at -5 ° C for 3 hours. By pouring on a mixture of 70 g Ice and 10 ml of hydrochloric acid, the reaction is stopped. The reaction mixture is taken twice extracted with 150 ml of diethyl ether, the organic phases twice with 70 ml of 2N Hydrochloric acid and washed twice with 100 ml of saturated sodium chloride solution, over Dried sodium sulfate and then evaporated. The residue obtained is from Recrystallized from ethanol / water; Mp .: 109-111 ° C.

Example 51 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) - pyrimidinyl] -benzaldehyde

To a suspension of 19.38 g of pyridinium chlorochromate in 250 ml of dichloromethane is added while stirring at room temperature for 30 minutes a solution of 20.08 g 2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) pyr imidinyl-] -benzyl alcohol added dropwise in 250 ml of dichloromethane and the reaction mixture for 3 hours stirred at 25-28 ° C. The clear solution is decanted, the brown residue with 100 ml of dichloromethane and the dichloromethane solution over 150 g of silica gel filtered. The filtrate is concentrated and the residue from n-hexane / ethyl acetate recrystallized; Mp .: 168-169 ° C.

C. Formulation Examples Example F1

To prepare a 25% wettable powder, the following listed ingredients mixed together:

weight Compound of formula I (active ingredient) 25 Hydrated silicic acid (carrier, grinding aids) 20 Sodium lauryl sulfate (wetting agent) 2 Sodium lignosulfonate (dispersing agent) 4 Kaolin (carrier)  49 100

It is first the liquid or molten drug in a grinder on the submitted submitted silicic acid. Subsequently, the other ingredients admixed. The mixture is made using a pin mill or similar Grinder finely ground.

The resulting wettable powder results in a fine suspension when stirred in water, the is suitable as a ready-to-use spray mixture.

Particularly suitable compounds for this formulation are compounds of the formula I which are liquid or have a low melting point, d. H. to about + 100 ° C, exhibit.

Example F2

High melting point compounds of formula I, i. H. from about + 100 ° C, may preferably be used as active ingredients in concentrated wettable powders, for example, as follows:

weight Compound of formula I (active ingredient) 75 Hydrated silicic acid (carrier, grinding aids) 1 Alkylnaphthalene sulfonate and alkyl carboxylate sulfate as sodium salts, for example, "Morowett EFW" (trade name of De Soto) (wetting agent) 2 Sulfonated naphthalene-formaldehyde condensate as sodium salt, for example "Morowett D-425" (trade name of De Soto) (dispersing agent) 10 Polyvinylpyrrolidone, for example PVP-K-30 (GAF Corp.) (binder) 1 Kaolin (carrier)  11 100

The ingredients are mixed together and using a pin mill or a comparable milling device, in particular a jet mill, fine ground.

When stirred into water, the resulting wettable powder gives a fine suspension any concentration that is suitable as a ready-to-use spray mixture.

Example F43

A wettable powder based on the composition of Example 4 can be converted into a dispersible granules. This is the ground powder in a suitable granulating device (for example granulating plate, mixing drum, Intensive mixer or fluidized bed granulator) with an aqueous solution of the binder sprayed until agglomerates have formed. After that, the added water removed again in a drying process. The granules of the desired size are screened out.

The resulting granules have various advantages over the spray powder (no Dust formation during application, easier dosing due to better flowability companies). The application is carried out after stirring the preparation in water and after complete disintegration of the granules into the primary particles exactly the same as Wettable powder.

Example F4

The compounds of formula I are in the usual organic Solvents limited solubility. Accordingly, emulsifiable concentrates of relatively low concentration possible; for example:

Compound of formula I (active ingredient) | 125 g / l "Sorprophor BSU" (trade name of Rhône-Poulenc) (emulsifier) 300 g / l N-methyl-2-pyrrolidone (solvent). ad 1000 ml

The active ingredient and the emulsifier are added with stirring to the solvent. The mixture is stirred until a homogeneous solution has formed.

The resulting emulsifiable concentrate can be emulsified in water and gives while a ready-spray mixture of the desired concentration.

Example F5

Compounds of formula I having a melting point above about + 60 ° C. also be formulated as so-called suspension concentrates ("flowables"); for example:

Compound of formula I (active ingredient) | 250 g / l Ethylene glycol (antifreeze) 80 g / l Silica (anti-settling agent) 5 g / l Xanthan gum., For example, "Kelzan" (trade name of Kelco) (thickener) 2 g / l Silicone antifoam, for example "Rhodorsil 426" (trade name of Rhône-Poulenc) 5 g / l Nonylphenol polyethoxylate (wetting agent) 20 g / l Sulfonated naphthalene-formaldehyde condensate as sodium salt, for example "Morowett D-425" (trade name of De Soto) (dispersing agent) 40 g / l Water, ad 1000 ml

The formulation auxiliaries are dissolved in water. In the solution, the pre-ground Active ingredient dispersed with stirring. The resulting coarse suspension will now subjected to wet grinding (for example in a colloid mill or a Stirred ball). Optionally, there are now other additives in small quantities possible, such as anti-foaming agents, anti-settling agents and biocides.

The resulting "Flowable" can be diluted as desired for use with water and gives a ready-to-use spray mixture of the desired concentration.  

D. Biological Examples Example B1: Pre-emergent herbicidal action

In the greenhouse, immediately after sowing, the test plants are placed in seed trays the earth's surface with an aqueous spray mixture corresponding to an application rate of 0.3 kg of active substance / hectare treated. The seed trays are in the greenhouse at 22-25 ° C and 50-70% relative humidity maintained.

After 4 weeks, the herbicidal action is treated with a multistage (10 = 100% Damage, 5 = 50% damage, 0 = no damage) Boniturschema in the comparison evaluated with an untreated control group.

In this experiment, the compounds of the formula I according to Examples 4, 5, 6, 7 and 8 strong herbicidal action.

Examples of the good herbicidal activity of the compound of formula I are the Table B1:

Table B1

Pre-eminent herbicidal action

Example B2: Post-emergent herbicidal action (contact herbicide)

A number of weeds, both monocotyledonous and dicotyledonous, were found to be leaking (in the 1- to 2-leaf stage) with an aqueous active ingredient dispersion in a dosage of 1 kg of active substance per hectare sprayed on the plants and this at 24 ° -26 ° C and 45-60% relative humidity maintained. 21 days after the treatment will be the  Verification 01830 00070 552 001000280000000200012000285910171900040 0002004237920 00004 01711uch having a multi-level rating system (10 = 100% damage, 0 = none Damage). Also in this experiment, the compounds of formula I show according to Examples 4, 5, 6, 7 and 8 good herbicidal action. Examples of the good herbicidal activity of the compounds of formula I are given in Table B2:

Table B2

Postemergent herbicidal action

Example B3: Herbicidal action for water rice (paddy)

The water weevil Echinochloa crus-galli is placed in plastic cups (60 cm² surface, 500 ml volume). After sowing, it gets to the surface with water refilled. 3 days after sowing, the water level will rise slightly above the surface of the earth increased (3-5 mm). The application takes place 3 days after the sowing by an injection of the Test substances on the vessels. The dose used corresponds to an amount of active ingredient of 3 kg AS per hectare. The plant cups are then housed in the greenhouse optimal growth conditions for the rice weeds, i. at 25 ° -30 ° C and high humidity.

The evaluation of the experiments takes place 3 weeks after application. The connections of the formula I according to Examples 4, 5, 6, 7 and 8 damage the weeds.

Claims (18)

1. 3-Aryluracil derivatives of the formula I. wherein -W- the group wherein the bond to the ring nitrogen atom is via the C atom;
R₁ is hydrogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃ or C₄ alkenyl or C₃ or C₄ alkynyl;
R₂ is halogen or cyano;
R₃ is hydrogen or halogen;
R₄ is hydrogen, halogen or C₁-C₄-alkyl;
R₅ is C₁-C₄ alkyl or C₁-C₄ haloalkyl; or R₄ and R₅ together are - (CH₂) _n -;
n is the number 3 or 4;
R₁₁ is C₁-C₄ alkyl, C₃ or C₄ alkenyl or C₃ or C₄ alkynyl; and
Q the group means
wherein R₆ and R₇ are independently hydrogen, C₁-C₈-alkyl, C₃-C₇-cycloalkyl or C₃-C₇-cycloalkyl-C₁-C₄-alkyl;
R₈ is halogen or a group -X₁-R₉ (2) in which
X₁ is oxygen, -S (O) _m -, -OSO₂- or -S-SO₂-;
R₉ is hydrogen, C₁-C₅-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₅-haloalkyl, C₂-C₅-alkenyl , C₂-C₅ alkynyl, optionally substituted aryl, optionally substituted benzyl or a group wherein
X₂ oxygen and sulfur; and
R₁₀ is hydrogen, C₁-C₅-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₅-haloalkyl, C₂-C₅-alkenyl , C₂-C₅-alkynyl, C₁-C₅-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₅-haloalkoxy, C₂-C₅-alkenyloxy, C₃-C₅-alkinyloxy, C₁-C₅-alkylthio, C₃ -C₅-alkenylthio, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted benzyloxy, optionally substituted benzylthio, optionally substituted aryl or optionally substituted benzyl;
m is the number 0, 1 or 2;
with the condition that in formula 2, if R₉ is hydrogen or the group X₁ is oxygen or sulfur; and if R₁ is hydrogen, and the agrochemically acceptable salts of compounds of formula I. 2. 3-aryluracil derivatives according to claim 1, characterized in that these of the formula Ia in which R₁, R₂, R₃, R₄, R₅ and Q have the meanings given in claim 1. 3. 3-Aryluracil derivatives according to claim 1, characterized in that these of the formula Ib in which R₂, R₃, R₄, R₅, R₁₁ and Q have the meanings given in claim 1. 4. 3-Aryluracil derivatives according to one of claims 1 or 2, wherein R₁ is C₁-C₄alkyl, C₁-C₄-haloalkyl, C₃- or C₄-alkenyl or C₃- or C₄-alkynyl means. 5. 3-Aryluracil derivatives according to any one of claims 1 to 4, wherein wherein R₆, R₇ and R₈ have the meaning given in claim 1. 6. 3-aryluracil derivatives according to claim 5, wherein R₆ and R₇ independently, hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁- or -C₂-alkyl; R₈ is halogen or a group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m , -OSO₂-; R₉ is hydrogen, C₁-C₃-alkyl, C₁- or C₂-alkoxy-C₁- or C₂-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁- or -C₂-alkyl, C₁-C₃-haloalkyl, C₃-C₅ alkenyl, C₃-C₅ alkynyl, optionally substituted aryl, optionally substituted benzyl, or a group in which R₁₀ is C₁-C₅-alkyl, C₁-C₃-alkoxy-C₁- or C₂-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁- or C₂-alkyl, C₁-C₃-haloalkyl, C₃- Alkenyl, Propargyl, C₁-C₃-alkoxy, C₁-C₃-alkoxy-C₁- or -C₂-alkoxy, C₁-C₃-haloalkoxy, C₂- or C₃-alkenyloxy, C₃-C₅-alkynyloxy, C₁-C₃-alkylthio, C₃ Alkenylthio, optionally substituted aryloxy, optionally substituted benzyloxy, optionally substituted arylthio, optionally substituted aryl or optionally substituted benzyl; m is the number 0, 1 or 2; with the condition that if R₉ is hydrogen or the group X₁ is oxygen or sulfur. 7. 3-aryluracil derivatives according to claim 6, wherein R₆ and R₇ independently, hydrogen, C₁-C₃-alkyl or C₃-C₆-cycloalkyl; R₈ is halogen or a group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m -, or -OSO₂-; m is the number 0, 1 or 2; R₉ is hydrogen, C₁-C₃ alkyl, allyl, propargyl, optionally substituted aryl or the group wherein R₁₀ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, allyl, propargyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃ alkenyloxy, propargyloxy or C₁-C₃ alkylthio. 8. 3-aryluracil derivatives according to claim 2, wherein R₁ is hydrogen, C₁-C₄-alkyl, C₃- or C₄-alkenyl or C₃- or C₄-alkynyl; R₂ is chlorine, bromine or cyano; R₃ is hydrogen or fluorine; R₄ is hydrogen, fluorine or methyl; R₅ is C₁-C₄ alkyl, trifluoromethyl or pentafluoroethyl; or R₄ and R₅ together are - (CH₂) _n -; and n is the number 3 or 4. 9. 3-aryluracil derivatives according to claim 8, wherein R₁ is hydrogen, methyl, allyl or propargyl; R₂ cyano, chlorine or bromine; R₄ is hydrogen or methyl; and R₅ methyl, Trifluoromethyl or pentafluoroethyl. 10. 3-Aryluracil derivatives according to claim 3, wherein R₂ is chlorine, bromine or cyano; R₃ is hydrogen or fluorine; R₄ is hydrogen, methyl or fluorine; R₅ is methyl, trifluoromethyl or pentafluoroethyl; and R₄ and R₅ together are - (CH₂) _n -; n is the number 3 or 4; R₁₁ C₁-C₂-alkyl, allyl or propargyl, means. 11. 3-aryluracil derivatives according to claim 10, wherein R₂ is chlorine; R₄ is hydrogen; R₅ Methyl, trifluoromethyl or pentafluoroethyl; and R₁₁ is methyl. 12. 3-aryluracil derivatives according to claim 1, wherein -W- the group means; R₁ is methyl; R₂ is cyano or chloro; R₃ is hydrogen or fluorine; R4 is hydrogen or methyl; R₅ is methyl, trifluoromethyl or pentafluoroethyl; or R₄ and R₅ together are - (CH₂) _n -; n is the number 3; and Q the group means; wherein R₆ and R₇ are independently hydrogen, C₁-C₅-alkyl or C₅- or C₆-cycloalkyl; R₈ is halogen or a group -X₁-R₉ (2), wherein X₁ is oxygen, -S (O) _m -, or -OSO₂-; R₉ is hydrogen, C₁-C₃ alkyl, allyl, propargyl, optionally substituted aryl or the group wherein R₁₀ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-alkenyloxy, propargyloxy or C₁-C₃ alkylthio; and m is the number 0, 1 or 2. 13. A compound according to claim 1 selected from the group:
2-propanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl) ester,
Isobutyric acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro-methyl-1 (2H) -pyrimidinyl] -benzyl) ester,
(2-Chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl) -isopropyl ether,
(2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -benzyl allyl ether, and
Methanesulfonic acid (2-chloro-5- [3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoro-methyl-1 (2H) -pyrimidinyl] -benzyl) ester. 14. Compounds of formula IIa or IIb wherein
R₂ is halogen or cyano;
R₃ is hydrogen or halogen;
R _{4 'is} hydrogen, fluorine or C₁-C₄-alkyl;
R₅ is C₁-C₄ alkyl or C₁-C₄ haloalkyl; or
R _{4 '} and R _5' together are - (CH₂) _n -;
R₅ is C₁-C₄ alkyl; or R₄ 'and R₅' together are - (CH₂) _n -;
n is the number 3 or 4;
R₁₂ C₁-C₆ alkyl, especially C₁-C₄ alkyl; and
Q 'the group in which
R₆ and R₇ are independently hydrogen, C₁-C₈ alkyl, C₃-C₇ cycloalkyl or C₃-C₇ cycloalkyl-C₁-C₄ alkyl;
X₁ is oxygen, or -S (O) _m ;
R _{9 'is} hydrogen, C₁-C₅-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₅-haloalkyl, C₂-C₅ Alkenyl, C₂-C₅ alkynyl, optionally substituted aryl, optionally substituted benzyl; and
m is 0, 1 or 2, with the proviso that when R _{9 'is} hydrogen, X 1 is oxygen or sulfur. 15. Compounds of the formula III wherein R₂, R₃, R₅, R₆ and R₇ have the meanings given in claim 14;
R₄ is hydrogen, halogen or C₁-C₄-alkyl; Y is chlorine or bromine; and Q "the group in which
R _{9 is "} C₁-C₅-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl,
C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₅-haloalkyl, C₂-C₅-alkenyl, C₂-C₅-alkynyl, optionally substituted aryl or optionally substituted benzyl; X₁ is oxygen or -S (O) _m -; and m is the number 0, 1 or 2. 16. A process for the preparation of compounds of the formula I according to claim 1, characterized in that a compound of the formula IIa or IIb under basic conditions to a salt of formula IIc or IId cyclized, wherein in the formulas IIa, IIb, IIc and IId, the radicals R₂, R₃, R _{4 '} , R₅, R _5' , R₁₂ and Q 'have the meanings given in claim 14, M₁ ^{⊕ is} a cation, and optionally the obtained salts in the presence of an acid in the compounds with R₁ hydrogen, or in the presence of an alkylating agent in the 3-aryluracil derivatives, wherein R₁ is C₁-C₄-alkyl, C₃- or C₄-alkenyl or C₃- or C₄-alkynyl, transferred , 17. weed control agent, characterized by a content of at least one  A compound of the formula I or salts thereof according to claim 1. 18. A method for controlling weeds, characterized in that the against weeds to be protected crops and / or the weeds with a Active ingredient of the formula I according to one of claims 1 to 13 or with a latter Agent containing active ingredient according to claim 17 treated.