1,2-Oxazolyl alkyl carbamates, and their use as herbicides

Abstract

1,2-Oxazolyl alkyl carbamates of the formula ##STR1## where R.sup.1 denotes alkyl of a maximum of 6 carbon atoms, alkoxyalkyl of a maximum of 3 carbon atoms, or alkoxycarbonyl of a maximum of 5 carbon atoms, R.sup.2 denotes hydrogen, or unsubstituted or halogen-substituted alkyl of a maximum of 3 carbon atoms, R.sup.3 denotes hydrogen, or alkyl of a maximum of 3 carbon atoms, and R.sup.4 denotes alkyl or cycloalkyl of a maximum of 6 carbon atoms, substituted or unsubstituted phenyl, or naphthyl, methylenedioxyphenyl, ethylenedioxyphenyl, benzofuranyl, dihydrobenzofuranyl or indanyl; the manufacture of such compounds, their use for combating unwanted plant growth, and herbicides containing these compounds.

Description

The present invention relates to 1,2-oxazolyl alkyl carbamates, a process for their manufacture, herbicides containing these compounds as active ingredients, and a process for combating unwanted plant growth with these compounds.

It is known that carbamates are suitable for combating unwanted plant growth. For instance, isopropyl N-phenylcarbamate combats grasses (German No. 833,274), the action being mainly via the roots. To bring the agent into contact with the roots, it is thus necessary for the soil to be adequately moist; consequently, the effectiveness of the herbicide depends on precipitation conditions.

Isopropyl N-3-chlorophenylcarbamate (U.S. Pat. No. 2,695,225) offers an improvement in herbicidal action on the preferred preemergence application. The use of methyl N-3,4-dichlorophenylcarbamate for combating unwanted plants on both pre- and postemergence application has also been disclosed (U.S. Pat. No. 3,116,995). The active ingredient is suitable for combating weeds in large-seed Leguminosae and rice, application being effected preemergence or soon after emergence when the plants are very small.

Furthermore, 1,2-oxazolylmethylthiol carbamates having a herbicidal action have been disclosed (German Laid-Open Application DE-OS No. 2,633,790). Compared with other prior art thiol carbamates, these compounds have a different and broader spectrum of action. Because their vapor pressure is low, they need not be incorporated into the soil before sowing.

We have now found that 1,2-oxazolyl alkyl carbamates of the formula ##STR2## where R.sup.1 is alkyl of a maximum of 6 carbon atoms, alkoxyalkyl of a maximum of 3 carbon atoms, or alkoxycarbonyl of a maximum of 5 carbon atoms, R.sup.2 denotes hydrogen, or unsubstituted or halogen-substituted alkyl of a maximum of 3 carbon atoms, R.sup.3 denotes hydrogen, or alkyl or a maximum of 3 carbon atoms, and R.sup.4 denotes alkyl or cycloalkyl of a maximum of 6 carbon atoms, phenyl which is unsubstituted or substituted by halogen, nitro, cyano, or alkyl, alkoxy, haloalkyl, haloalkoxy, alkanoyl or alkoxycarbonyl of a maximum of 5 carbon atoms, or by cycloalkyl of a maximum of 6 carbon atoms, or R.sup.4 denotes naphthyl, methylenedioxyphenyl, ethylenedioxyphenyl, benzofuranyl, dihydrobenzofuranyl or indanyl, have a herbicidal action on both pre- and postemergence application and are at the same time tolerated by crop plants. They have an action superior to that of prior art herbicidal (thiol) carbamates on broadleaved unwanted plants.

In formula I, R.sup.1 denotes linear or branched alkyl of a maximum or 6, preferably a maximum of 4, carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1-methyl-n-butyl, n-hexyl, and 1-methyl-n-pentyl, linear or branched alkoxyalkyl of a maximum of 3 carbon atoms, such as methoxymethyl and methoxyethyl, or alkoxycarbonyl of a maximum of 5, especially a maximum of 4, carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and the 4 isomeric butoxycarbonyl radicals; R.sup.2 denotes, in addition to hydrogen, unsubstituted or halogen-substituted alkyl of a maximum of 3 carbon atoms, such as methyl, chloromethyl, ethyl, 2-chloroethyl, n-propyl and isopropyl; R.sup.3 denotes, in addition to hydrogen, alkyl of a maximum of 3 carbon atoms, such as methyl, ethyl and propyl; and R.sup.4 denotes linear or branched alkyl of a maximum of 6, especially a maximum of 4, carbon atoms, such as methyl, ethyl, isopropyl and the 4 isomeric butyl radicals, cycloalkyl of a maximum of 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, unsubstituted phenyl or phenyl which is mono- or polysubstituted by halogen, nitro, cyano, linear or branched alkyl, alkoxy, haloalkyl, haloalkoxy, alkanoyl or alkoxycarbonyl, each of a maximum of 5, especially of a maximum of 3, carbon atoms, or by cycloalkyl of from 3 to 6 carbon atoms, such as 3-chlorophenyl, 3,4-dichlorophenyl, 3-fluoro-4-chlorophenyl, 4-fluorophenyl, 3-chloro-4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 2,5-difluorophenyl, 3-nitro-4-methylphenyl, 3-chloro-4-cyanophenyl, 3-chloro-4-methylphenyl, 3-methylphenyl, 2-isopropylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 3,4-dimethylphenyl, 2-ethylphenyl, 2,6-diethylphenyl, 3-trifluoromethylphenyl, 3-trifluoromethyl-4-chlorophenyl, 2-methyl-3-chlorophenyl, 2-methoxy-4-chlorophenyl, 2,4-dimethoxy-5-chlorophenyl, 4-methoxy-3-chlorophenyl, 4-difluoromethoxyphenyl, 3-methoxy-4-methylphenyl, 4-cyclopropylphenyl, 4-cyclohexylphenyl, 4-acetylphenyl, 4-propionylphenyl, 4-methoxycarbonylphenyl, 4-ethoxycarbonylphenyl, and 3-ethoxycarbonylphenyl; R.sup.4 may further denote naphthyl, indanyl, benzofuranyl, 1,2-methylenedioxyphenyl, 1,2-ethylenedioxyphenyl and 2,3-dihydrobenzofuranyl.

The 1,2-oxazolyl alkyl carbamates of the formula I are obtained by reaction of 5-hydroxymethyl-1,2-oxazoles of the formula ##STR3## where R.sup.1, R.sup.2 and R.sup.3 have the above meanings, with isocyanates of the formula

OCN--R.sup.4 III, where R.sup.4 has the above meanings, in the presence of absence of a diluent.

The reaction is carried out at a temperature of from -50.degree. to +150.degree. C., preferably from +20.degree. to 60.degree. C. It may be advantageous to employ a diluent and a catalyst.

Suitable solvents are aromatic and aliphatic, optionally chlorinated, hydrocarbons, such as benzene, toluene, cresols, halobenzenes, methylene chloride, chloroform, and carbon tetrachloride, ethers, such as diethyl ether, tetrahydrofuran, and dioxane, ketones, such as diethyl ketone, methyl ethyl ketone, and diisopropyl ketone, and acetonitrile, dimethylformamide and dimethyl sulfoxide. Suitable catalysts are tertiary amines, such as triethylamine.

Some of the 5-hydroxymethyl-1,2-oxazoles of the formula II employed as starting materials are known; they may be prepared on the basis of prior art processes (Tetrahedron Letters, 4, 327-330, 1967). For instance the following 5-hydroxymethyl-1,2-oxazoles of the formula II are obtained in this manner:

______________________________________ ##STR4##R.sup.1 R.sup.2 R.sup.3 n.sub.D.sup.25 /b.p.______________________________________CH.sub.3 H H 1.4773CH.sub.3 H CH.sub.3 1.4721C.sub.2 H.sub.5 H H 95-100.degree. C./0.27 mbarC.sub.2 H.sub.5 H CH.sub.3 92-93.degree. C./0.13 mbarCH.sub.3 OCH.sub.2 H H 1.4778CH.sub.3 OCH.sub.2 H CH.sub.3 118-121.degree. C./1.1 mbarn-C.sub.3 H.sub.7 H H 1.4738n-C.sub.3 H.sub.7 H CH.sub.3 1.4673sec-C.sub.4 H.sub.9 H CH.sub.3 1.4742n-C.sub.4 H.sub.9 H CH.sub.3 1.4692C.sub.2 H.sub.5 OOC H CH.sub.3 1.4740CH.sub.3 CH.sub.2 Cl H 1.4862t-C.sub.4 H.sub.9 H H 1.4725t-C.sub.4 H.sub.9 H CH.sub.3 1.4786i-C.sub.4 H.sub.9 H CH.sub.3 1.4735i-C.sub.4 H.sub.9 H CH.sub.3 119-125.degree. C./0.67 mbarsec-C.sub.4 H.sub.9 H H 1.4742______________________________________

The isocyanates of the formula OCN--R.sup.4 are known or may be readily prepared by known methods (Houben-Weyl, Methoden der organ. Chemie, 8, 119-128, Georg Thieme-Verlag, Stuttgart, 1952).

The 1,2-oxazolyl alkyl carbamates of the formula I according to the invention may be prepared analogously to the following example.

EXAMPLE 1

13.5 parts by weight of 3-isobutyl-5-(1'-hydroxyethyl)-1,2-oxazole is dissolved in 150 parts by volume of toluene; after the addition of 0.1 part by weight of triethylamine, 9.5 parts by weight of phenyl isocyanate is added dropwise. The mixture is then stirred for 1 hour at room temperature and for 4 hours at 50.degree. C. After the mixture has cooled, the precipitate is filtered and washed with petroleum ether. There is obtained 14 parts by weight of 1-(3-isobutyl-1,2-oxazol-5-yl)-ethyl-N-phenyl carbamate as a crystalline substance; melting point: 105.degree. C.

______________________________________C.sub.16 H.sub.20 N.sub.2 O.sub.3 (288) C H N______________________________________calc.: 66.7 7.0 9.7found: 66.7 6.5 10.3______________________________________

For instance the following compounds of the formula ##STR5## may be obtained analogously:

__________________________________________________________________________ m.p. (.degree.C.)/.delta.-valuesNo. R.sup.1 R.sup.2 R.sup.3 R.sup.4 (MHz; LM)__________________________________________________________________________2 i-C.sub.4 H.sub.9 H CH.sub.3 ##STR6## 97-1013 i-C.sub.4 H.sub.9 H CH.sub.3 ##STR7## 106-1094 CH.sub.3 OCH.sub.2 H H ##STR8## [80; D.sub.6 DMSO] 2.3 (3H); 4.5 (2H), 5.3 (2H), 6.1 (1H), 6.7-7.4 (4H)5 CH.sub.3 OCH.sub.2 H H ##STR9## 84-856 n-C.sub.3 H.sub.7 H CH.sub.3 ##STR10## 68-707 n-C.sub.3 H.sub.7 H CH.sub.3 ##STR11## 60-638 n-C.sub.3 H.sub.7 H CH.sub.3 ##STR12## 83-869 sec-C.sub.4 H.sub.9 H CH.sub.3 ##STR13## 74-7610 sec-C.sub.4 H.sub.9 H CH.sub.3 ##STR14## 85-8711 sec-C.sub.4 H.sub.9 H CH.sub.3 ##STR15## 102-10412 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR16## [100; D.sub.6 DMSO] 1.7 (3H), 3.3 (3H), 4.45 (2H), 6.0 (1H), 6.5 (1H), 6.9-7.6 (4H)13 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR17## [100; D.sub.6 DMSO] 1.45 (3H), 2.3 (3H), 3.3 (3H), 4.42 (2H), 5.96 (1H), 6.5 (1H), 6.7-7.3 (4H)14 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR18## [100; D.sub.6 DMSO] 6.9 (3H), 1.1-1.7 (4H), 1.6 (3H), 2.6 (3H), 5.94 (1H), 6.4 (1H), 6.8- 7.5 (5H), 9.8 (1H)15 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR19## [220; D.sub.6 DMSO] 0.9 (3H), 1.3 (2H), 1.45-1.7 (2 + 3H), 4.25 (3H), 2.55 (2H), 5.95 (1H), 6.4 (1H), 6.8 (1H), 7.1-7.3 (3H), 4.8 (1H)16 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR20## [220; D.sub.6 DMSO] 0.9 (3H), 1.35 (2H), 1.5-1.7 (2H + 3H), 2.6 (2H), 5.96 (1H), 6.45 (1H), 7.05 (1H), 7.25-7.7 (3H), 10.2 (1H)17 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR21## [220; D.sub.6 DMSO] 0.9 (3H), 1.35 (2H), 1.5-1.7 (3H + 2H), 2.6 (2H), 6.05 (1H), 6.5 (1H), 7.3-8.0 (4H), 10.3 (1H)18 H.sub.5 C.sub.2 OOC H CH.sub.3 ##STR22## 59-6119 H.sub.5 C.sub.2 OOC H CH.sub.3 ##STR23## 103-10420 H.sub.5 C.sub.2 OOC H CH.sub.3 ##STR24## 143-14421 H.sub.5 C.sub.2 OOC H CH.sub.3 ##STR25## 104-10622 CH.sub.3 H CH.sub.3 ##STR26## 10923 C.sub.2 H.sub.5 H CH.sub.3 ##STR27## 107-11024 t-C.sub.4 H.sub.9 H CH.sub.3 ##STR28## 112-11425 t-C.sub.4 H.sub.9 H CH.sub.3 ##STR29## 86-8726 t-C.sub.4 H.sub.9 H CH.sub.3 ##STR30## 86-8727 t-C.sub.4 H.sub.9 H CH.sub.3 ##STR31## [100; D.sub.6 DMSO] 1.3 (9H), 1.65 (3H), 5.98 (1H), 5.6 (1H), 7.3-7.8 (3H)28 t-C.sub.4 H.sub.9 H CH.sub.3 ##STR32## 102-10529 t-C.sub.4 H.sub.9 H CH.sub.3 C.sub.6 H.sub.11 88-9230 CH.sub.3 H CH.sub.3 ##STR33## 120-12331 CH.sub.3 H CH.sub.3 ##STR34## [60; D.sub.6 DMSO] 1.63 (3H), 2.25 (3H), 5.95 (1H), 6.4 (1H), 7.2-7.8 (3H)32 t-C.sub.4 H.sub.9 H CH.sub.3 ##STR35## 122-12333 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR36## [60; D.sub.6 DMSO] 1.6 (3H), 3.3 (3H), 4.4 (2H), 5.9 (1H), 6.2 (1H), 6.9-7 (5H), 7.7 (1H)34 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR37## [270; CDCl.sub.3 + D.sub.6 DMSO] 1.74 (3H), 3.25 (3H), 4.45 (2H), 6.05 (1H), 6.32 (1H), 7.18 (2H), 7.75 (1H), 8.44 (1H)35 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR38## [60; D.sub.6 DMSO] 1.5 (3H), 3.15 (3H), 4.35 (2H), 5.9 (1H), 6.45 (1H), 6.8-7.5 (4H), 9.8 (1H)36 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR39## [60; D.sub.6 DMSO] 1.65 (3H), 3.2 (3H), 4.36 (2H), 5.9 (1H), 6.47 (1H), 7.2-7.85 (4H)37 CH.sub.3 H CH.sub.3 i-C.sub.3 H.sub.7 [60; CDCl.sub.3 ] 1.16 (6H), 1.6 (3H), 2.25 (3H), 3.8 (1H), 5.3 (1H), 5.9 (1H), 6.1 (1H)38 CH.sub.3 H CH.sub.3 CH.sub.3 [60; CDCl.sub.3 ] 1.55 (3H), 2.25 (3H), 2.75 (3H), 5.7 (1H), 5.85 (1H), 6.05 (1H)39 C.sub.2 H.sub.5 H CH.sub.3 ##STR40## 7840 C.sub.2 H.sub.5 H CH.sub.3 ##STR41## 8341 C.sub.2 H.sub.5 H CH.sub.3 ##STR42## 5442 C.sub.2 H.sub.5 H CH.sub.3 ##STR43## 7243 C.sub.2 H.sub.5 H CH.sub.3 ##STR44## 74-7544 C.sub.2 H.sub.5 H CH.sub.3 ##STR45## 6745 C.sub.2 H.sub.5 H CH.sub.3 ##STR46## 73-7646 CH.sub.3 H CH.sub.3 ##STR47## 99-10047 CH.sub.3 H CH.sub.3 ##STR48## 107-10848 CH.sub.3 H CH.sub.3 ##STR49## 91-9349 CH.sub.3 H CH.sub.3 ##STR50## 83-8450 CH.sub.3 H CH.sub.3 ##STR51## 12351 CH.sub.3 H CH.sub.3 ##STR52## 52-5652 CH.sub.3 H CH.sub.3 ##STR53## 110-11353 CH.sub.3 H CH.sub.3 ##STR54## 6254 CH.sub.3 H CH.sub.3 ##STR55## 95-9855 CH.sub.3 H CH.sub.3 C.sub.5 H.sub.9 40-4256 CH.sub.3 H CH.sub.3 ##STR56## 62-6757 CH.sub.3 H CH.sub.3 ##STR57## 79-8258 i-C.sub.3 H.sub.7 H CH.sub.3 ##STR58## 113-11459 CH.sub.3 H CH.sub.3 ##STR59## 98-10060 CH.sub.3 H CH.sub.3 ##STR60## 56.6061 C.sub.2 H.sub.5 H CH.sub.3 ##STR61## 87-8862 t-C.sub.4 H.sub.9 CH.sub.2 Cl H ##STR62## [60; CDCl.sub.3 ] 1.35 (9H), 3.95 (2H), 4.64 (2H), 6.6-7.4 (5H)63 t-C.sub.4 H.sub.9 CH.sub.2 Cl H ##STR63## [100; D.sub.6 DMSO] 1.45 (9H), 2.3 (3H), 4.53 (2H), 4.9 (2H), 7.3 (2H), 7.42 (1H)64 t-C.sub.4 H.sub.9 H H ##STR64## 92-9665 t-C.sub. 4 H.sub.9 CH.sub.2 Cl H ##STR65## [60; D.sub.6 DMSO] 1.4 (9H), 4.5 (2H), 4.83 (2H), 6.4-7.6 (4H)66 CH.sub.3 H H ##STR66## [60; D.sub.6 DMSO] 2.1-2.2 (6H), 5.2 (2H), 6.32 (1H), 6.7-7.3 (4H)67 CH.sub.3 H H ##STR67## [100; D.sub.6 DMSO] 2.24 (3H), 5.32 (2H), 6.5 (1H), 7.3-8.0 (4H)68 CH.sub.3 CH.sub.2 Cl H ##STR68## [60; CDCl.sub.3 ] 2.11 (3H), 2.24 (3H), 4.1 (2H), 4.78 (2H), 6.8-7.4 (5H)69 CH.sub.3 H H ##STR69## [100; D.sub.6 DMSO] 2.28 (3H), 5.3 (2H), 6.5 (1H), 7.0-7.7 (4H)70 CH.sub.3 H H ##STR70## [60; D.sub.6 DMSO] 2.23 (3H), 5.3 (2H), 6.4 (1H), 6.9-7.6 (5H), 9.82 (1H)71 C.sub.2 H.sub.5 H H ##STR71## 100-10272 t-C.sub.4 H.sub.9 H H ##STR72## 157-15873 C.sub.2 H.sub.5 H H ##STR73## [60; CDCl.sub.3 ] 1.2 (3H), 2.6 (2H), 5.2 (2H), 6.14 (1H), 6.9-7.5 (5H), 7.95 (1H)74 C.sub.2 H.sub.5 H H ##STR74## [60; CDCl.sub.3 ] 1.27 (3H), 2.7 (2H), 5.25 (2H), 6.22 (1H), 7.1-7.4 (4H), 8.2 (1H)75 C.sub.2 H.sub.5 H H ##STR75## [60; D.sub.6 DMSO] 1.3 (3H), 2.72 (2H), 5.38 (2H), 6.5 (1H), 6.9-7.2 (4H), 10.05 (1H)76 CH.sub.3 CH.sub.2 Cl H ##STR76## [60; D.sub.6 DMSO] 2.1 (3H), 4.4 (2H), 4.8 (2H), 7.3 (2H), 7.6 (1H), 10.1 (1H)77 C.sub.2 H.sub.5 CH.sub.2 Cl H ##STR77## [60; DCDl.sub.3 ] 1.2 (3H), 2.5 (2H), 4.1 (2H), 4.8 (2H), 6.9-7.7 (6H), 8.1 (1H)78 C.sub.2 H.sub.5 CH.sub.2 Cl H ##STR78## [60; CDCl.sub.3 ] 1.18 (3H), 2.5 (2H), 4.0 (2H), 4.7 (2H), 6.0-7.7 (4H)79 CH.sub.3 CH.sub.2 Cl H ##STR79## [60; CDCl.sub.3 ] 2.2 (3H), 4.1 (2H), 4.75 (2H), 7.1-7.8 (4H)80 CH.sub.3 H CH.sub.3 ##STR80## [60; CDCl.sub.3 ] 1.6 (3H), 2.2 (3H), 5.9 (1H), 6.04 (1H), 7.2-7.9 (5H)81 CH.sub.3 H CH.sub.3 ##STR81## [60; CDCl.sub.3 ] 1.5 (3H), 2.2 (3H), 5.87 (1H), 5.92 (1H), 6.7-7.4 (5H)82 CH.sub.3 H CH.sub.3 ##STR82## [60; CDCl.sub.3 ] 1.52 (3H), 1.68 (3H), 5.9 (1H), 5.97 (1H), 6.9-7.5 (6H)83 t-C.sub.4 H.sub.9 H H ##STR83## 8484 t-C.sub.4 H.sub.9 H H ##STR84## 140-14185 t-C.sub.4 H.sub.9 H H ##STR85## 80-8386 CH.sub.3 H CH.sub.3 ##STR86## 101-10587 CH.sub.3 H CH.sub.3 ##STR87## 92-9388 CH.sub.3 H CH.sub.3 ##STR88## 72-7589 C.sub.2 H.sub.5 H CH.sub.3 C.sub.6 H.sub.11 7390 CH.sub.3 H CH.sub.3 ##STR89## [60; CDCl.sub.3 ] 1.45 (3H), 2.1 (6H), 5.7-6.0 (2H), 6.95 (2H), 7.2-7.4 (2H)91 CH.sub.3 H CH.sub.3 ##STR90## [60; CDCl.sub.3 ] 1.52 (3H), 2.15 (3H), 5.7-6.1 (2H), 6.5-7.4 (4H), 7.76 (1H)92 CH.sub.3 H CH.sub.3 ##STR91## [60; CDCl.sub.3 ] 1.5 (3H), 2.3 (3H), 5.9-6.2 (2H), 7.2-7.5 (4H)93 CH.sub.3 H CH.sub.3 ##STR92## [60; CDCl.sub.3 ] 1.3 (3H), 1.65 (3H), 2.3 (3H), 2.6 (2H), 5.9-6.2 (2H), 6.7 (1H), 7.1-7.9 (4H)94 CH.sub.3 H CH.sub.3 C.sub.6 H.sub.11 [60; CDCl.sub.3 ] 0.9-1.9 (10H), 1.45 (3H), 2.05 (3H), 3.3 (1H), 4.9 (1H), 5.1-6.0 (2H)95 CH.sub.3 H CH.sub.3 ##STR93## [60; CDCl.sub.3 ] 1.5 (3H), 2.15 (2H), 5.7-6.0 (2H), 6.35 (1H), 6.8-7.5 (5H)96 CH.sub.3 H CH.sub.3 ##STR94## [60; CDCl.sub.3 ] 1.5 (3H), 2.0 (3H), 2.1 (6H), 5.7-6.0 (2H), 6.35 (1H), 6.7-7.5 (3H)97 CH.sub.3 H CH.sub.3 ##STR95## [60; CDCl.sub.3 ] 1.76 (3H), 2.2 (2H), 2.4 (3H), 3.0 (4H), 5.9-6.3 (2H), 7.1-7.5 (4H)98 CH.sub.3 H CH.sub.3 ##STR96## [60; D.sub.6 DMSO] 1.55 (3H), 2.16 (6H), 5.85 (1H), 6.2 (1H), 6.6-7.3 (4H), 9.6 (1H)99 CH.sub.3 H CH.sub.3 ##STR97## [60; D.sub.6 DMSO] 1.63 (3H), 2.2 (3H), 5.95 (1H), 6.3 (1H), 7.2-7.8 (3H), 10.1 (1H)100 CH.sub.3 H CH.sub.3 ##STR98## [60; D.sub.6 DMSO] 1.6 (3H), 2.2 (3H), 5.92 (1H), 6.3 (1H), 6.8-7.6 (4H), 10.05 (1H)101 CH.sub.3 H CH.sub.3 ##STR99## [60; CDCl.sub.3 ] 1.6 (3H), 2.1 (3H), 2.2 (3H), 3.7 (3H), 5.8-6.1 (2H), 6.75-7.2 (3H), 7.7 (1H)102 CH.sub.3 H CH.sub.3 ##STR100## [60; CDCl.sub.3 ] ? (9H), 1.4 (3H), 2.2 (3H), 5.8-6.1 (2H), 7.1-7.3 (5H)103 C.sub.2 H.sub.5 H CH.sub.3 ##STR101## [60; CDCl.sub.3 ] 1.2 (3H), 1.6 (3H), 2.65 (2H), 5.7-6.2 (2H), 6.9-7.5 (6H)104 CH.sub.3 H CH.sub.3 ##STR102## [60; CDCl.sub.3 ] 1.6 (3H), 2.2 (3H), 5.7-6.2 (2H), 7.2-7.8 (3H), 7.96 (1H)105 CH.sub.3 CH.sub.2 Cl H ##STR103## [60; CDCl.sub.3 ] 2.1 (6H), 4.1 (2H), 4.7 (2H), 7.1-7.6 (4H)106 i-C.sub.4 H.sub.9 H CH.sub.3 ##STR104## 58-62__________________________________________________________________________

The active ingredients according to the invention may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure a fine distribution of the active ingredient.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, ddimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

Examples of formulations are given below.

I. 90 parts by weight of compound 1 is mixed with 10 parts by weight of N-methyl-.alpha.-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound 2 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound 37 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

IV. 20 parts by weight of compound 4 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210.degree. and 280.degree. C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

V. 20 parts by weight of compound 5 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound 20 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound 96 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 20 parts of compound 11 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The active ingredients or agents containing them may be applied pre- or postemergence, either to the location before the unwanted plants have germinated from seed or sprouted from vegetative plant parts, or to the leaves of the unwanted and crop plants. A special application technique is to spray the active ingredients with the aid of spraying equipment in such a way that the leaves of sensitive crop plants are if possible not hit; the active ingredients reach the soil or unwanted plants growing below the crop plants (post-directed, lay-by treatment). Application rates depend on the time of the year and the growth stage, and vary from 0.1 to 15 kg/ha and more, the higher rates being particularly suitable for the total elimination of vegetation.

The influence of various representatives of the 1,2-oxazolyl alkyl carbamates according to the invention on the growth of unwanted and crop plants is demonstrated in the following greenhouse experiments.

The vessels employed were plastic flowerpots having a volume of 300 cm.sup.3 and which were filled with a sandy loam containing about 1.5% humus. The seeds of the test plants (cf. Table 1) were sown shallow, and separately, according to species. For the preemergence treatment, the active ingredients were applied to the surface of the soil immediately after the seeds has been sown. The compounds were emulsified or suspended in water as vehicle, and sprayed through finely distributing nozzles. After the agents had been applied, the vessels were lightly sprinkler-irrigated to induce germination and growth and to activate the chemical agents. Transparent plastic covers were then placed on the vessels until the plants had taken root. The cover ensured uniform germination of the plants, insofar as this was not impaired by the chemicals.

For the postemergence treatment, the plants were first grown in the vessels to a height of from 3 to 10 cm, depending on growth form, before being treated. No cover was placed on the vessels.

The pots were set up in the greenhouse-species from warmer areas at from 25.degree. to 40.degree. C., and species from moderate climates at 15.degree. to 30.degree. C. The experiments were run for from 3 to 6 weeks. During this period, the plants were tended and their reactions to the various treatments assessed. Tables 2 to 12 contain the compounds investigated and the application rates in kg/ha of active ingredient. The plants used for the tests are given in Table 1. The scale used for assessment was 0 to 100, 0 denoting no damage or normal emergence, and 100 denoting nonemergence or complete destruction of at least the visible plant parts.

TABLE 1______________________________________List of plant namesBotanical name Abbreviation in tables Common name______________________________________Allium cepa -- onionAlopecurus myosuroides Alopec. myos. slender foxtailArachys hypogaea Arachys hyp. groundnutsAvena fatua -- wild oatsBeta vulgaris -- sugarbeetsBrassica napus -- rapeBromus spp. -- bromeCassia spp. --Centaurea cyanus Cent. cyan. cornflowerChenopodium album Chenopod. alb. lambsquartersDatura stramonium -- jimsonweedDaucus carota -- carrotsDesmodium tortuosumGlycine max -- soybeansLolium multiflorum -- Italian ryegrassMatricaria spp. Matric. spp. chamomileNicandra physaloides Nicand. phys. apple-of-PeruSesbania exaltata Sesbania exalt. hemp sesbaniaSinapis alba -- white mustardSorghum bicolor Sorgh. bicol. wild caneSolanum nigrum Solan. nigr. black nightshadeStellaria media -- chickweedTriticum aestivum Tritic. aest. wheatMercurialis annua Mercur. ann. annual mercuryOryza sativa Oryza sat. rice______________________________________ TABLE 2______________________________________Herbicidal action on Lolium multiflorum;preemergence application in the greenhouse ##STR105## %Active damageingre- at a ratedient of 3.0 kgno. R.sup.1 R.sup.2 R.sup.3 R.sup.4 a.i./ha______________________________________98 CH.sub.3 H CH.sub.3 ##STR106## 10082 CH.sub.3 H CH.sub.3 ##STR107## 10081 CH.sub.3 H CH.sub.3 ##STR108## 10091 CH.sub.3 H CH.sub.3 ##STR109## 100103 C.sub.2 H.sub.5 H CH.sub.3 ##STR110## 10039 C.sub.2 H.sub.5 H CH.sub. 3 ##STR111## 10041 C.sub.2 H.sub.5 H CH.sub.3 ##STR112## 10044 C.sub.2 H.sub.5 H CH.sub.3 ##STR113## 10053 CH.sub.3 H CH.sub.3 ##STR114## 10058 i-C.sub.3 H.sub.7 H CH.sub.3 ##STR115## 10031 CH.sub.3 H CH.sub.3 ##STR116## 10033 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR117## 10035 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR118## 10068 CH.sub.3 CH.sub.2 Cl H ##STR119## 10070 CH.sub.3 H H ##STR120## 10077 C.sub.2 H.sub.5 CH.sub.2 Cl H ##STR121## 10062 tert.-C.sub. 4 H.sub.9 CH.sub.2 Cl H ##STR122## 10065 tert.-C.sub.4 H.sub.9 CH.sub.2 Cl H ##STR123## 1005 CH.sub.3OCH.sub.2 H H ##STR124## 956 n-C.sub.3 H.sub.7 H CH.sub.3 ##STR125## 959 sec-C.sub.4 H.sub.9 H CH.sub.3 ##STR126## 1001 i-C.sub.4 H.sub.9 H CH.sub.3 ##STR127## 1007 n-C.sub.3 H.sub.7 H CH.sub.3 ##STR128## 9013 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR129## 10014 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR130## 10015 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR131## 10016 n-C.sub.4 H.sub.9 H CH.sub.3 ##STR132## 100______________________________________ TABLE 3__________________________________________________________________________Selective control of Alopecurus myosuroides insugarbeets;preemergence application in the greenhouse Test plants and % damageActive Alopecurusingredient Appl. rate Beta myosuroi-no. Formula kg a.i./ha vulgaris des__________________________________________________________________________98 ##STR133## 1.0 0 100 ##STR134## 1.0 0 70 (German 833,274) ##STR135## 1.0 40 100 (U.S. Pat. No. 2,695,225)__________________________________________________________________________ TABLE 4______________________________________Postemergence action on Lolium multiflorum in thegreenhouse ##STR136##Activeingre- % damagedient at a rate ofno. R.sup.1 R.sup.2 R.sup.3 R.sup.4 3.0 kg a.i./ha______________________________________100 CH.sub.3 H CH.sub.3 ##STR137## 10098 CH.sub.3 H CH.sub.3 ##STR138## 10082 CH.sub.3 H CH.sub.3 ##STR139## 100103 C.sub.2 H.sub.5 H CH.sub.3 ##STR140## 10039 C.sub.2 H.sub.5 H CH.sub.3 ##STR141## 10040 C.sub.2 H.sub.5 H CH.sub.3 ##STR142## 10041 C.sub.2 H.sub.5 H CH.sub.3 ##STR143## 10044 C.sub.2 H.sub.5 H CH.sub.3 ##STR144## 10053 CH.sub.3 H CH.sub.3 ##STR145## 10031 CH.sub.3 H CH.sub.3 ##STR146## 10036 CH.sub.3 OCH.sub.2 H CH.sub.3 ##STR147## 10068 CH.sub.3 CH.sub.2 Cl H ##STR148## 10077 C.sub.2 H.sub.5 CH.sub.2 Cl H ##STR149## 10062 tert-C.sub.4 H.sub.9 CH.sub.2 Cl H ##STR150## 100______________________________________ TABLE 5______________________________________Postemergence action on Sinapis alba in the greenhouse ##STR151##Activeingre- % damagedient at a rate ofno. R.sup.1 R.sup.2 R.sup.3 R.sup.4 3.0 kg a.i./ha______________________________________86 CH.sub.3 H CH.sub.3 ##STR152## 10090 CH.sub.3 H CH.sub.3 ##STR153## 10082 CH.sub.3 H CH.sub.3 ##STR154## 10081 CH.sub.3 H CH.sub.3 ##STR155## 10080 CH.sub.3 H CH.sub.3 ##STR156## 10093 CH.sub.3 H CH.sub.3 ##STR157## 10092 CH.sub.3 H CH.sub.3 ##STR158## 10095 CH.sub.3 H CH.sub.3 ##STR159## 10041 C.sub.2 H.sub.5 H CH.sub.3 ##STR160## 10044 C.sub.2 H.sub.5 H CH.sub.3 ##STR161## 10053 CH.sub.3 H CH.sub.3 ##STR162## 10056 CH.sub.3 H CH.sub.3 ##STR163## 10037 CH.sub.3 H CH.sub.3 i-C.sub.3 H.sub.7 10038 CH.sub.3 H CH.sub.3 CH.sub.3 100105 CH.sub.3 CH.sub.2 Cl H ##STR164## 10077 C.sub.2 H.sub.5 CH.sub.2 Cl H ##STR165## 100______________________________________ TABLE 6__________________________________________________________________________Selective herbicidal action; postemergence treatment in the greenhouseActive Appln. Test plants and % damageingre- rate Gly- Cas- Des-dient (kg a.i./ Arachys cine Sorgh. sia modium Nicand Sesban.no. Formula ha) hyp. max bicol. spp. tort. phys. exalt.__________________________________________________________________________34 ##STR166## 1.0 0 10 10 90 100 100 100 ##STR167## 1.0 10 20 15 0 100 20 60 (U.S. Pat. No. 3,116,995) ##STR168## 1.0 10 30 25 0 30 0 10 (German Laid-Open Application DE-OS 2,633,790)__________________________________________________________________________ TABLE 7__________________________________________________________________________Selective action in carrots; postemergence treatment in the greenhouseActive Test plants and % damageingredient Appln. rate Daucus Chenopod. Desmod. Sinapisno. Formula (kg a.i./ha) carota alb. tort. alba__________________________________________________________________________36 ##STR169## 1.0 0 99 95 90 ##STR170## 1.0 10 20 10 80 (U.S. Pat. No. 2,695,225)__________________________________________________________________________ TABLE 8__________________________________________________________________________Selective herbicidal action; postemergence treatment in the greenhouseActive Appln. Test plants and % damageingre- rate Ara- Mat-dient (kg a.i./ chys Tritic. Cent. ric. Nicand. Sinapis Solan.no. Formula ha) hyp. aest. cyan. spp. phys. alba nigr.__________________________________________________________________________35 ##STR171## 1.0 0 0 80 100 100 98 100 ##STR172## 1.0 10 80 -- 0 0 80 50 (U.S. Pat. No. 2,695,225) ##STR173## 1.0 10 70 -- 0 0 20 70 (German Laid-Open Application DE-OS 2,633,790)__________________________________________________________________________ TABLE 9______________________________________Selective control of unwanted grasses and broadleavedweeds;postemergence treatment in the greenhouse ##STR174## (No. 33) % damage atTest plants 2.0 kg a.i/ha______________________________________Allium cepa 0Beta vulgaris 0Alopecurus myosuroides 90Avena fatua 80Bromus spp. 90Centaurea cyanus 80Datura stramonium 80Sinapis alba 100Stellaria media 90______________________________________ TABLE 10__________________________________________________________________________Selective control of grassy weeds in rape; postemergence treatmentin the greenhouse Test plants and % damageActive Appln. rate Brassica Alopec.ingredient no. (kg a.i./ha) napus myos. Avena fatua__________________________________________________________________________98 ##STR175## 1.0 0 100 90 ##STR176## 1.0 80 90 80 (U.S. Pat. No. 2,695,225)__________________________________________________________________________ TABLE 11__________________________________________________________________________Selective control of Chenopodium album in sugarbeets and other crops;postemergence treatment in the greenhouse ##STR177##Active Test plants and % damageingredient kg/ha Arachys Beta Oryza Chenop.no. X R a.i. hyp. vulg. sat. album__________________________________________________________________________13 CH.sub.3 CH.sub.2OCH.sub.3 1.0 0 0 10 100 2.0 0 0 10 10021 CF.sub.3 COOC.sub.2 H.sub.5 0.5 0 0 0 100 1.0 0 10 0 100__________________________________________________________________________ 0 = no damage 100 = plants destroyed TABLE 12__________________________________________________________________________Selective weed control; postemergence application in the greenhouseActive Test plants and % damageingre- Ara- Gly- Mer-dient kg/ha chys cine Sorghum Chenop. Datura Desmod. cur.no. Structure a.i. hyp. max bicolor album stram. tort. ann.__________________________________________________________________________12 ##STR178## 0.5 0 0 0 100 100 100 90__________________________________________________________________________ 0 = no damage 100 = plants destroyed

In view of the many application methods possible, the agents according to the invention, or mixtures containing them, may be used in addition to the crop plants listed in the tables in a large number of other crops for eliminating unwanted growth.

The following crop plants are given by way of example:

______________________________________Botanical name Common name______________________________________Allium cepa onionsAnanas comosus pineapplesArachis hypogaea peanuts (groundnuts)Asparagus officinalis asparagusAvena sativa oatsBeta vulgaris spp. altissima sugarbeetsBeta vulgaris spp. rapa fodder beetsBeta vulgaris spp. esculenta table beets, red beetsBrassica napus var. napus rapeBrassica napus var. napobrassicaBrassica napus var. rapa turnipsBrassica rapa var. silvestrisCamellia sinensis tea plantsCarthamus tinctorius safflowerCarya illinoinensis pecan treesCitrus limon lemonsCitrus maxima grapefruitsCitrus reticulata mandarinsCitrus sinensis orange treesCoffea arabica (Coffea canephora,Coffea liberica) coffee plantsCucumis melo melonsCucumis sativus cucumbersCynodon dactylon Bermudagrass in turf and lawnsDaucus carota carrotsElais guineensis oil palmsFragaria vesca strawberriesGlycine max soybeansGossypium hirsutum(Gossypium arboreum cottonGossypium herbaceumGossypium vitifolium)Helianthus annuus sunflowersHelianthus tuberosusHevea brasiliensis rubber plantsHordeum vulgare barley Humulus lupulus hopsIpomoea batatas sweet potatoesJuglans regia walnut treesLactuca sativa lettuceLens culinaris lentilsLinum usitatissimum flaxLycopersicon lycopersicum tomatoesMalus spp. apple treesManihot esculenta cassavaMedicago sativa alfalfa (lucerne)Mentha piperita peppermintMusa spp. banana plantsNicothiana tabacum tobacco(N. rustica)Olea europaea olive treesOryza sativa ricePanicum miliaceumPhaseolus lunatus limabeansPhaseolus mungo mungbeansPhaseolus vulgaris snapbeans, green beans, dry beansPennisetum glaucumPetroselinum crispum parsleyspp. tuberosumPicea abies Norway spruceAbies alba fir treesPinus spp. pine treesPisum sativum English peasPrunus avium cherry treesPrunus domestica plum treesPrunus dulcis almond treesPrunus persica peach treesPyrus communis pear treesRibes sylvestre redcurrantsRibes uva-crispaRicinus communisSaccharum officinarum sugar caneSecale cereale ryeSesamum indicum sesameSolanum tuberosum Irish potatoesSorghum bicolor (s. vulgare) grain sorghumSorghum dochnaSpinacia oleracea spinachTheobroma cacao cacao plantsTrifolium pratense red cloverTriticum aestivum wheatVaccinium corymbosum blueberriesVaccinium vitis-idaea cranberriesVicia faba tick beansVigna sinensis (V. unguiculata) cow peasVitis vinifera grapesZea mays Indian corn, sweet corn, maize______________________________________

The new 1,2-oxazolyl alkyl carbamates according to the invention may, in addition to admixture among themselves, be mixed and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable mixture components are diazines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, phenoxy fatty acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, etc. Such combinations broaden the spectrum of action and synergistic effects are sometimes achieved. A number of active ingredients which, when combined with the new compounds, give mixtures useful for widely varying applications are given below by way of example:

5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone 5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone 5-amino-4-chloro-2-cyclohexyl-3(2H)-pyridazinone 5-amino-4-bromo-2-cyclohexyl-3(2H)-pyridazinone 5-methylamino-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone 5-methylamino-4-chloro-2-(3-.alpha.,.alpha.,.beta.,.beta.-tetrafluoroethoxyphenyl)-3(2H)-pyridazinone 5-dimethylamino-4-chloro-2-phenyl-3(2H)-pyridazinone 4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone 4,5-dimethoxy-2-cyclohexyl-3(2H)-pyridazinone 4,5-dimethoxy-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone 5-methoxy-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone 5-amino-4-bromo-2(3-methylphenyl)-3(2H)-pyridazinone 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts 3-(1-methylethyl)-8-chloro-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts 3-(1-methylethyl)-8-fluoro-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts 3-(1-methylethyl)-8-methyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts 1-methoxymethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-methoxymethyl-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-methoxymethyl-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-cyano-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-cyano-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-cyano-8-methyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-cyano-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 1-azidomethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 3-(1-methylethyl)-1H-pyridino-[3,2-e]-2,1,3-thiadiazin-(4)-one-2,2-dioxide N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethylaniline N-(1-methylethyl)-N-ethyl-2,6-dinitro-4-trifluoromethylaniline N-n-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline N-n-propyl-N-cyclopropylmethyl-2,6-dinitro-4-trifluoromethylaniline N-bis-(n-propyl)-2,6-dinitro-3-amino-4-trifluoromethylaniline N-bis-(n-propyl)-2,6-dinitro-4-methylaniline N-bis-(n-propyl)-2,6-dinitro-4-methylsulfonylaniline N-bis-(n-propyl)-2,6-dinitro-4-aminosulfonylaniline bis-(.beta.-chloroethyl)-2,6-dinitro-4-methylaniline N-ethyl-N-(2-methylallyl)-2,6-dinitro-4-trifluoromethylaniline 3,4-dichlorobenzyl N-methylcarbamate 2,6-di-tert.butyl-4-methylphenyl N-methylcarbamate isopropyl N-phenylcarbamate 3-methoxyprop-2-yl N-3-fluorophenylcarbamate isopropyl N-3-chlorophenylcarbamate but-1-yn-3-yl N-3-chlorophenylcarbamate 4-chlorobut-2-yn-1-yl N-3-chlorophenylcarbamate methyl N-3,4-dichlorophenylcarbamate methyl N-(4-aminobenzenesulfonyl)-carbamate O-(N-phenylcarbamoyl)-propanone oxime N-ethyl-2-(phenylcarbamoyl)-oxypropionic acid amide 3'-N-isopropylcarbamoyloxypropionaniline ethyl-N-(3-(N'-phenylcarbamoyloxy)-phenyl)-carbamate methyl-N-(3-(N'-methyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate isopropyl-N-(3-(N'-ethyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate methyl-N-(3-(N'-3-methylphenylcarbamoyloxy)-phenyl)-carbamate methyl-N-(3-(N'-4-fluorophenylcarbamoyloxy)-phenyl)-carbamate methyl-N-(3-(N'-3-chloro-4-fluorophenylcarbamoyloxy)-phenyl)-carbamate ethyl-N-[3-N'-(3-chloro-4-fluorophenylcarbamoxyloxy)-phenyl]-carbamate ethyl-N-[3-N'-(3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate methyl-N-[3-(N'-3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylcarbamate ethyl N-3-(2'-methylphenoxycarbonylamino)-phenylcarbamate methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylthiolcarbamate methyl N-3-(2',4',5'-trimethylphenoxycarbonylamino)-phenylthiolcarbamate methyl N-3-(phenoxycarbonylamino)-phenylthiolcarbamate p-chlorobenzyl N,N-diethylthiolcarbamate ethyl N,N-di-n-propylthiolcarbamate n-propyl N,N-di-n-propylthiolcarbamate 2,3-dichloroallyl N,N-diisopropylthiolcarbamate 2,3,3-trichloroallyl, N,N-diisopropylthiolcarbamate 3-methyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate 3-ethyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate ethyl N,N-di-sec.-butylthiolcarbamate benzyl N,N-di-sec.-butylthiolcarbamate ethyl N-ethyl-N-cyclohexylthiolcarbamate ethyl N-ethyl-N-bicyclo-[2.1.1]-heptylthiolcarbamate S-(2,3-dichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate S-(2,3,3-trichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate S-ethylhexahydro-1-H-azepine-1-carbothiolate S-benzyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate S-benzyl-(2,3-dimethylhexahydro-1-H-azepine-1)-carbothiolate S-ethyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate n-propyl N-ethyl-N-n-butylthiolcarbamate 2-chloroallyl N,N-dimethyldithiocarbamate N-methyldithiocarbamic acid, sodium salt trichloroacetic acid, sodium salt .alpha.,.alpha.-dichloropropionic acid, sodium salt .alpha.,.alpha.-dichlorobutyric acid, sodium salt .alpha.,.alpha.-.beta.,.beta.-tetrafluoropropionic acid, sodium salt .alpha.-methyl-.alpha.,.beta.-dichloropropionic acid, sodium salt methyl .alpha.-chloro-.beta.-(4-chlorophenyl)-propionate methyl .alpha.,.beta.-dichloro-.beta.-phenylpropionate benzamido oxyacetic acid 2,3,5-triiodobenzoic acid (salts, esters, amides) 2,3,6-trichlorobenzoic acid (salts, esters, amides) 2,3,5,6-tetrachlorobenzoic acid (salts, esters, amides) 2-methoxy-3,6-dichlorobenzoic acid (salts, esters, amides) 2-methoxy-3,5,6-trichlorobenzoic acid (salts, esters, amides) 3-amino-2,5,6-trichlorobenzoic acid (salts, esters, amides) O,S-dimethyltetrachlorothioterephthalate dimethyl-2,3,5,6-tetrachloroterephthalate disodium 3,6-endoxohexahydrophthalate 4-amino-3,5,6-trichloropicolinic acid (salts) ethyl 2-cyano-3-(N-methyl-N-phenyl)-aminoacrylate isobutyl 2-[4-(4'-chlorophenoxy)-phenoxy]-propionate methyl 2-[4-(2',4'-dichlorophenoxy)-phenoxy]-propionate methyl 2-[4-(4'-trifluoromethylphenoxy)-phenoxy]-propionate 2-[4-(2'-chloro-4'-trifluorophenoxy)-phenoxy]-propionic acid, sodium salt 2-[4-(3',5'-dichloropyridyl-2-oxy)-phenoxy]-propionic acid, sodium salt ethyl 2-(N-benzoyl-3,4-dichlorophenylamino)-propionate methyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate isopropyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-chloro-4-ethylamino-6-(amino-2'-propionitrile)-1,3,5-triazine 2-chloro-4-ethylamino-6-(2-methoxypropyl)-2-amino-1,3,5-triazine 2-chloro-4-ethylamino-6-butyn-1-yl-2-amino-1,3,5-triazine 2-chloro-4,6-bisethylamino-1,3,5-triazine 2-chloro-4,6-bisisopropylamino-1,3,5-triazine 2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine 2-azido-4-methylamino-6-isopropylamino-1,3,5-triazine 2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-methylthio-4-ethylamino-6-tert.butylamino-1,3,5-triazine 2-methylthio-4,6-bisethylamino-1,3,5-triazine 2-methylthio-4,6-bisisopropylamino-1,3,5-triazine 2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-methoxy-4,6-bisethylamino-1,3,5-triazine 2-methoxy-4,6-bisisopropylamino-1,3,5-triazine 4-amino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one 4-amino-6-phenyl-3-methyl-4,5-dihydro-1,2,4-triazin-5-one 4-isobutylidenamino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one 1-methyl-3-cyclohexyl-6-dimethylamino-1,3,5-triazin-2,4-dione 3-tert.butyl-5-chloro-6-methyluracil 3-tert.butyl-5-bromo-6-methyluracil 3-isopropyl-5-bromo-6-methyluracil 3-sec.butyl-5-bromo-6-methyluracil 3-(2-tetrahydropyranyl)-5-chloro-6-methyluracil 3-(2-tetrahydropyranyl)-5,6-trimethyleneuracil 3-cyclohexyl-5,6-trimethyleneuracil 2-methyl-4-(3'-trifluoromethylphenyl)-tetrahydro-1,2,4-oxadiazine-3,5-dione 2-methyl-4-(4'-fluorophenyl)-tetrahydro-1,2,4-oxadiazine-3,5-dione 3-amino-1,2,4-triazole 1-allyloxy-1-(4-bromophenyl)-2-[1',2',4'-triazolyl-(1')]-ethane (salts) 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,3-triazol-1-yl)-butan-2-one N,N-diallylchloroacetamide N-isopropyl-2-chloroacetanilide N-(but-1-yn-3-yl)-2-chloroacetanilide 2-methyl-6-ethyl-N-propargyl-2-chloroacetanilide 2-methyl-6-ethyl-N-ethoxymethyl-2-chloroacetanilide 2-methyl-6-ethyl-N-(2-methoxy-1-methylethyl)-2-chloroacetanilide 2-methyl-6-ethyl-N-(isopropoxycarbonylethyl)-2-chloroacetanilide 2-methyl-6-ethyl-N-(4-methoxypyrazol-1-yl-methyl)-2-chloro-acetanilide 2-methyl-6-ethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide 2,6-dimethyl-N-(pyrazon-1-yl-methyl)-2-chloroacetanilide 2,6-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-2-chloro-acetanilide 2,6-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-2-chloroacetanilide 2,6-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-2-chloroacetanilide 2,6-dimethyl-N-(1,3-dioxolan-2-yl-methyl)-2-chloroacetanilide 2,6-dimethyl-N-(2-methoxyethyl)-2-chloroacetanilide 2,6-dimethyl-N-isobutoxymethyl-2-chloroacetanilide 2,6-diethyl-N-methoxymethyl-2-chloroacetanilide 2,6-diethyl-N-n-butoxymethyl-2-chloroacetanilide 2,6-diethyl-N-ethoxycarbonylmethyl-2-chloroacetanilide 2,3,6-trimethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide 2,3-dimethyl-N-isopropyl-2-chloroacetanilide 2-(2-methyl-4-chlorophenoxy-N-methoxyacetamide 2-(.alpha.-naphthoxy)-N,N-diethylpropionamide 2,2-diphenyl-N,N-dimethylacetamide .alpha.-(3,4,5-tribromopyrazol-1-yl)-N,N-dimethylpropionamide N-(1,1-dimethylpropynyl)-3,5-dichlorobenzamide N-1-napthylphthalamic acid propionic acid 3,4-dichloroanilide cyclopropanecarboxylic acid 3,4-dichloroanilide methacrylic acid 3,4-dichloroanilide 2-methylpentanecarboxylic acid 3,4-dichloroanilide N-2,4-dimethyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide N-4-methyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide 2-propionylamino-4-methyl-5-chlorothiazole O-(methylsulfonyl)-glycolic acid N-ethoxymethyl-2,6-dimethylanilide O-(methylaminosulfonyl)-glycolic acid N-isopropylanilide O-(isopropylaminosulfonyl)-glycolic acid N-but-1-yn-3-yl-anilide O-(methylaminosulfonyl)-glycolic acid hexamethyleneamide 2,6-dichlorothiobenzamide 2,6-dichlorobenzonitrile 3,5-dibromo-4-hydroxybenzonitrile (salts) 3,5-diiodo-4-hydroxybenzonitrile (salts) 3,5-dibromo-4-hydroxy-O-2,4-dinitrophenylbenzaldoxime (salts) 3,5-dibromo-4-hydroxy-O-2-cyano-4-nitrophenylbenzaldoxime (salts) pentachlorophenol, sodium salt 2,4-dichlorophenyl-4'-nitrophenyl ether 2,4,6-trichlorophenyl-4'-nitrophenyl ether 2-fluoro-4,6-dichlorophenyl-4'-nitrophenyl ether 2-chloro-4-trifluoromethylphenyl-4'-nitrophenyl ether 2,4'-dinitro-4-trifluoromethyl-diphenyl ether 2,4-dichlorophenyl-3'-methoxy-4'-nitro-phenyl ether 2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitro-phenyl ether 2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitro-phenyl ether (salts) 2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitro-phenyl ether 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione 2-(3-tert.butylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione 2-(3-isopropylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione 2-phenyl-3,1-benzoxazinone-(4) (4-bromophenyl)-3,4,5,9,10-pentaazatetracyclo-[5,4,1,0.sup.2,6, 0,.sup.8,11 ]-dodeca-3,9-diene 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyldimethylaminosulfate 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-(N-methyl-N-acetyl)-aminosulfonate 3,4-dichloro-1,2-benzisothiazole N-4-chlorophenyl-allylsuccinimide 2-methyl-4,6-dinitrophenol (salts, esters) 2-sec.butyl-4,6-dinitrophenol (salts, esters) 2-sec.butyl-4,6-dinitrophenol acetate 2-tert.butyl-4,6-dinitrophenol acetate 2-tert.butyl-4,6-dinitrophenol (salts) 2-tert.butyl-5-methyl-4,6-dinitrophenol (salts) 2-tert.butyl-5-methyl-4,6-dinitrophenol acetate 2-sec.amyl-4,6-dinitrophenol (salts, esters) 1-(.alpha.,.alpha.-dimethylbenzyl)-3-(4-methylphenyl)-urea 1-phenyl-3-(2-methylcyclohexyl)-urea 1-phenyl-1-benzoyl-3,3-dimethylurea 1-(4-chlorophenyl)-1-benzoyl-3,3-dimethylurea 1-(4-chlorophenyl)-3,3-dimethylurea 1-(4-chlorophenyl)-3-methyl-3-but-1-yn-3-yl-urea 1-(3,4-dichlorophenyl)-3,3-dimethylurea 1-(3,4-dichlorophenyl)-1-benzoyl-3,3-dimethylurea 1-(3,4-dichlorophenyl)-3-methyl-3-n.butylurea 1-(4-isopropylphenyl)-3,3-dimethylurea 1-(3-trifluoromethylphenyl)-3,3-dimethylurea 1-(.alpha.,.alpha.,.beta.,.beta.-tetrafluoroethoxyphenyl)-3,3-dimethylurea 1-(3-tert.butylcarbamoyloxyphenyl)-3,3-dimethylurea 1-(3-chloro-4-methylphenyl)-3,3-dimethylurea 1-(3-chloro-4-methoxyphenyl)-3,3-dimethylurea 1-(3,5-dichloro-4-methoxyphenyl)-3,3-dimethylurea 1-[4-(4'-chlorophenoxy)-phenyl]-3,3-dimethylurea 1-[4-(4'-methoxyphenoxy)-phenyl]-3,3-dimethylurea 1-cyclooctyl-3,3-dimethylurea 1-(hexahydro-4,7-methanoindan-5-yl)-3,3-dimethylurea 1-[1- or 2-(3a,4,5,7,7a-hexahydro)-4,7-methanoindanyl]-3,3-dimethylurea 1-(4-fluorophenyl)-3-carboxymethoxy-3-methylurea 1-phenyl-3-methyl-3-methoxyurea 1-(4-chlorophenyl)-3-methyl-3-methoxyurea 1-(4-bromophenyl)-3-methyl-3-methoxyurea 1-(3,4-dichlorophenyl)-3-methyl-3-methoxyurea 1-(3-chloro-4-bromophenyl)-3-methyl-3-methoxyurea 1-(3-chloro-4-isopropylphenyl)-3-methyl-3-methoxyurea 1-(3-chloro-4-methoxyphenyl)-3-methyl-3-methoxyurea 1-(3-tert.butylphenyl)-3-methyl-3-methoxyurea 1-(2-benzthiazolyl)-1,3-dimethylurea 1-(2-benzthiazolyl)-3-methylurea 1-(5-trifluoromethyl-1,3,4-thiadiazolyl)-1,3-dimethylurea imidazolidin-2-one-1-carboxylic acid isobutylamide 1,2-dimethyl-3,5-diphenylpyrazolium-methylsulfate 1,2,4-trimethyl-3,5-diphenylpyrazolium-methylsulfate 1,2-dimethyl-4-bromo-3,5-diphenylpyrazolium-methylsulfate 1,3-dimethyl-4-(3,4-dichlorobenzoyl)-5-(4-methylphenylsulfonyloxy)-pyrazole 2,3,5-trichloropyridinol-(4) 1-methyl-3-phenyl-5-(3'-trifluoromethylphenyl)-pyridone-(4) 1-methyl-4-phenylpyridinium chloride 1,1-dimethylpyridinium chloride 3-phenyl-4-hydroxy-6-chloropyridazine 1,1'-dimethyl-4,4'-dipyridylium-di(methylsulfate) 1,1'-di-(3,5-dimethylmorpholine-carbonylmethyl)-4,4'-dipyridylium dichloride 1,1'-ethylene-2,2'-dipyridylium dibromide 3-[1-(N-ethoxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-2,4-dione 3-[1-(N-allyloxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-2,4-dione 2-[1-(N-allyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1,3-dione (salts) 2-[1-(N-allyloxyamino-butylidene]-5,5-dimethylcyclohexane-1,3-dione (salts) 2-[1-(N-allyloxyamino-butylidene]-5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1,3-dione (salts) 2-chlorophenoxyacetic acid (salts, esters, amides) 4-chlorophenoxyacetic acid (salts, esters, amides) 2,4-dichlorophenoxyacetic acid (salts, esters, amides) 2,4,5-trichlorophenoxyacetic acid (salts, esters, amides) 2-methyl-4-chlorophenoxyacetic acid (salts, esters, amides) 3,5,6-trichloro-2-pyridinyl-oxyacetic acid (salts, esters, amides) methyl .alpha.-naphthoxyacetate 2-(2-methylphenoxy)-propionic acid (salts, esters, amides) 2-(4-chlorophenoxy)-propionic acid (salts, esters, amides) 2-(2,4-dichlorophenoxy)-propionic acid (salts, esters, amides) 2-(2,4,5-trichlorophenoxy)-propionic acid (salts, esters, amides) 2-(2-methyl-4-chlorophenoxy)-propionic acid (salts, esters, amides) 4-(2,4-dichlorophenoxy)-butyric acid (salts, esters, amides) 4-(2-methyl-4-chlorophenoxy)-butyric acid (salts, esters, amides) cyclohexyl-3-(2,4-dichlorophenoxy)-acrylate 9-hydroxyfluorenecarboxylic acid-(9) (salts, esters) 2,3,6-trichlorophenylacetic acid (salts, esters) 4-chloro-2-oxobenzothiazolin-3-yl-acetic acid (salts, esters) gibelleric acid (salts) disodium methylarsonate monosodium salt of methylarsonic acid N-phosphonomethyl-glycine (salts) N,N-bis-(phosphonomethyl)-glycine (salts) 2-chloroethyl 2-chloroethanephosphonate ammonium-ethyl-carbamoyl-phosphonate di-n-butyl-1-n-butylamino-cyclohexyl-phosphonate trithiobutylphosphite O,O-diisopropyl-5-(2-benzosulfonylaminoethyl)-phosphorodithionate 2,3-dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxide 5-tert.butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolone-(2) 4,5-dichloro-2-trifluoromethylbenzimidazole (salts) 1,2,3,6-tetrahydropyridazine-3,6-dione (salts) succinic acid mono-N-dimethylhydrazide (salts) (2-chloroethyl)-trimethylammonium chloride (2-methyl-4-phenylsulfonyl)-trifluoromethanesulfone anilide 1,1-dimethyl-4,6-diisopropyl-5-indanyl ethyl ketone 2-[1-(2,5-dimethylphenyl)-ethylsulfonyl]-pyridine-N-oxide sodium chlorate ammonium thiocyanate calcium cyanamide.

It may also be useful to apply the compounds according to the invention in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral matters used to remedy nutritional or trace element deficiencies. Oils of various types, oil concentrates, wetting agents, spreader-stickers and antifoams may be added to the individual active ingredients or mixtures thereof.

Claims

1. A 1,2-oxazolyl alkyl carbamate of the formula ##STR179## where R.sup.1 is alkoxyalkyl of a maximum of 3 carbon atoms, or alkoxycarbonyl of a maximum of 5 carbon atoms, R.sup.2 denotes hydrogen, or unsubstituted or halogen-substituted alkyl of a maximum of 3 carbon atoms, R.sup.3 denotes hydrogen, or alkyl of a maximum of 3 carbon atoms, and R.sup.4 denotes phenyl which is mono- or polysubstituted by halogen, nitro, cyano, linear or branched alkyl, alkoxy, haloalkyl, haloalkoxy, alkanoyl or alkoxycarbonyl, each of a maximum of 5 carbon atoms, or by cycloalkyl of from 3 to 6 carbon atoms.

2. A process for combating the growth of unwanted plants, wherein a herbicide is used which consists essentially of a 1,2-oxazolyl alkyl carbamate of the formula I as defined in claim 1.

3. 1-(3-Methoxymethyl-1,2-oxazol-5-yl)-ethyl-N-(3-chlorophenyl)-carbamate.

4. 1-(3-Methoxymethyl-1,2-oxazol-5-yl)-ethyl-N-(3-methylphenyl)-carbamate.

5. 1-(3-Methoxymethyl-1,2-oxazol-5-yl)-ethyl-N-(3-trifluoromethylphenyl)-carbamate.

6. A compound of the formula I as defined in claim 1 wherein R.sup.1 is methoxymethyl.

7. A herbicide consisting essentially of a carrier and a herbicidally effective amount of at least one 1,2-oxazolyl alkyl carbamate of the formula I as defined in claim 1.