WO1993011669A1

WO1993011669A1 - Use of 3-phenyluracil derivatives for the desiccation and abscission of plant parts

Info

Publication number: WO1993011669A1
Application number: PCT/EP1992/002772
Authority: WO
Inventors: Ralf Klintz; Peter Schaefer; Elisabeth Heistracher; Klaus Grossmann; Matthias Gerber
Original assignee: Basf Aktiengesellschaft
Priority date: 1991-12-10
Filing date: 1992-12-01
Publication date: 1993-06-24
Also published as: DE4140661A1; CN1075716A; AU3083792A

Abstract

The invention concerns the use, for the desiccation and abscission of plant organs, of 3-phenyluracil derivatives of the formula (I), in which R1 = H, alkyl, haloalkyl, formyl, alkanoyl, alkenyl or alkinyl; R2 = -CO-NR7R8 or -CO-R9 (in which R7 to R9 are as defined in the description) or a group bound by -O-, -O-CO-, -O-CS- or -O-SO¿2-; R?3 = halogen or CN; R4 = H or halogen; R5 = H, halogen or alkyl and R6 = alkyl or haloalkyl or R5 + R6 = tri- or tetramethylene; as well as the enol ethers of such compounds of formula (I) in which R1 is C1-C4 alkyl, C2-C5 alkenyl or C3-C5 alkinyl provided that R2 = -CO-O-CH¿2?-CH2-ON=C(R?12,R13¿) (in which R?12 and R13 = C¿1-C4 alkyl) or a group bound by -O-SO2-, as well as the agriculturally useful salts and enol ethers of such compounds of formula (I) in which R1 = hydrogen.

Description

Use of 3-phenylurazil derivatives for desiccation and

Removal of parts of plants Description

The present invention relates to the use of 3-phenylurazil derivatives of the general formula I.

where the variables have the following meaning:

R ^{1 is} hydrogen, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, the formyl group, a C ₂ -C ₆ alkanoyl group, a C ₃ -C ₄ alkenyl group or a C ₃ -C ₄ - Alkynyl group; R ^{2 is} a group bonded via -O-, -O-CO-, -O-CS- or -O-SO ₂ -, a group -CO-NR ⁷ R ⁸ or -CO-R ⁹ ;

R ³ halogen or cyano; R ^{4 is} hydrogen or halogen;

R ^{5 is} hydrogen, halogen or a C ₁ -C ₄ alkyl group;

R ^{6 is} a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group, or

R ⁵ and R ⁶ together form a tri- or tetramethylene chain, R ⁷ , R ⁸ - hydrogen, a C ₁ -C ₈ -alkyl radical which can also carry one of the following substituents: cyano, nitro, hydroxyl,

Hydroxycarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkoxycarbonyl, C ₁ -C ₄ alkylsulfonyl or the like

Di (C ₁ -C ₄ alkyl) phosphono; - A C ₂ -C ₈ alkenyl radical, a C ₃ -C ₈ alkynyl radical, one

C ₁ -C ₈ haloalkyl, a C ₃ -C ₈ cycloalkyl, a C ₁ -C ₈ alkoxy; - The phenyl radical or a phenyl-C ₁ -C ₄ -alkyl radical, where in each case a saturated five- to seven-membered ring with optionally 1 or 2 oxygen atoms as ring members can be fused to the phenyl ring, and wherein the phenyl rings if desired also one to can carry three substituents selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl,

C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy, hydroxyl, hydroxycarbonyl and C ₂ -C ₅ alkoxycarbonyl; with the proviso that R ⁷ and R ⁸ do not both simultaneously represent a C ₁ -C ₈ alkoxy radical, or R ⁷ and R ⁸ together with the common nitrogen atom form a four- to seven-membered heterocyclic ring which still contains one to three C ₁ - C ₆ -alkyl groups, one of the ring members being substituted by -O-, -S-, -N =, -NH- or -N (C ₁ -C ₄ -alkyl) -; R ^{9 is} a radical -OC (R ¹⁰ , R ¹¹ ) -CH ₂ -ON = C (R ¹² , R ¹³ ), -O-CH ₂ -ON = C (R ¹² , R ¹³ ), -O-Ν = C (R ¹⁴ , R ¹⁵ ), -OR ¹⁶ or -SR ¹⁷ ,

where R ^{9 is} not -OC (R ¹⁰ , R ¹¹ ) -CH ₂ -ON = C (R ¹² , R ¹³ ), -O-CH ₂ -ON = C (R ¹² , R ¹³ ) or -ON = C ( R ¹⁴ , R ¹⁵ ) may mean if R ^{1 is} hydrogen;

R ^{10 represents} hydrogen or C ₁ -C ₄ alkyl,

R ¹¹ denotes hydrogen, C ₁ -C ₄ alkyl, phenyl or benzyl,

R ^{12 represents} hydrogen or C ₁ -C ₆ alkyl,

R ¹³ denotes C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl or phenyl, or

R ¹² and R ¹³ together represent a three- to six-membered group

Alkylene chain, R ¹⁴ denotes C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylthio, C ₂ -C ₇ alkoxycarbonyl or C ₂ -C ₇ alkoxycarbonyl-C ₁ -C ₄ alkyl; R ¹⁵ denotes C ₁ -C ₆ alkyl, trifluoromethyl, C ₃ -C ₆ cycloalkyl,

C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxy-C ₁ -C ₄ alkyl,

C ₂ -C ₇ alkylcarbonyl, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₇ alkoxycarbonyl-C ₁ -C ₄ alkyl, di- (C ₂ -C ₇ alkoxycarbonyl) -C ₁ -C ₄ - alkyl, phenyl or 2-furyl, or

R ¹⁴ and R ¹⁵ together with the common carbon atom to which they are attached represent a cyclopentane or cyclohexane ring which, if desired, can carry one to 3 C ₁ -C ₄ alkyl groups;

R ^{16 represents} C ₁ -C ₈ haloalkyl, C ₃ -C ₅ haloalkenyl or

C ₃ -C ₅ haloalkynyl or - [C (R ¹⁸ , R ¹⁹ )] _m -Q, where the substituents R ¹⁸ and R ¹⁹ independently of one another are hydrogen or C ₁ -C ₃ alkyl, m is 0.1 or 2 and

Q for

- C ₃ -C ₇ cycloalkyl or a saturated three- to seven-membered heterocycle with one or two oxygen or

Sulfur atoms or an oxygen and a sulfur atom as heteroatoms and, if desired, a carbonyl group as a ring member, where the cycles on each substitutable carbon atom can carry a C ₁ -C ₄ alkyl group, or - phenyl, which can carry one to three radicals if desired from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and

C ₁ -C ₄ alkylthio, and where the phenyl ring can also carry a fused-on five- to seven-membered carbocyclic ring or a fused-on heterocyclic ring with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms;

R ¹⁷ denotes hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ alkenyl,

C ₃ -C ₈ alkynyl, C ₂ -C ₆ alkoxyalkyl, C ₃ -C ₈ cycloalkyl, which, if desired, can also carry one to 3 C ₁ -C ₄ alkyl groups, phenyl or benzyl; as well as the enol ethers of those compounds I in which R ¹ denotes a C ₁ -C ₄ alkyl, C ₂ -C ₅ alkenyl or C ₃ -C ₅ alkynyl group, unless R ² denotes a group above -O -SO ₂ - bound group or a group -CO-O-CH ₂ -CH ₂ -ON = C (R ¹² , R ¹³ ) with R ¹² and R ¹³ C ₁ -C ₄ alkyl, and the agriculturally useful salts and Enol ethers of those compounds of the formula I in which R ^{1 is} hydrogen for the desiccation and removal of plant organs.

Furthermore, the invention relates to a method for desiccating and cutting off plant organs, in particular the leaves, by means of the 3-phenylurazil derivatives I.

Unless R ¹ is C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl and R ^{2 is} a group bonded via -O-, -O-CO-, -O-CS- or -O-SO ₂ - , the compounds of the formula I are known (for example from EP-A 255 047, EP-A 260 621, WO 88/10254, WO 89/02891, WO 89/03825, WO 91/07392 and WO 91/07393). For these known 3-phenylurazil derivatives, a herbicidal or pesticidal activity is stated, but no defoliation activity.

From the U.S. 4,943,309 is the use of 3-pyrimidinylbenzoic acid derivatives of the formula II

I

where the substituents have the following meaning:

X oxygen or sulfur; R ^{a is} hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl or formyl;

R ^{b is} hydrogen, alkyl, alkenyl, alkynyl or alkoxyalkyl; R ^c halogen or nitro; R ^{d is} hydrogen or halogen;

R ^{e is} hydrogen, halogen, alkyl, chloromethyl, bromomethyl, alkoxymethyl, alkylthiomethyl, cyano, nitro or thiocyano;

R ^{f is} hydrogen, alkyl or fluoroalkyl or

R ^e and R ^f are optionally substituted by alkyl

Tri or tetramethylene chain, or a chain

- (CH ₂ ) _1-2 -Z- (CH ₂ ) _1-2 with Z oxygen or sulfur, known for defoliation of cotton.

The use of compounds of the 3-phenylurazil derivative I type for defoliation and / or desiccation can also be found in EP-A 408 382, WO 90/15057 and WO 91/00278.

Both abscess and desiccation agents are economically strong to make harvesting easier

Interest. Especially in intensive cotton cultivation

Use of defoliants required for the effective use of picking machines for capsule harvesting. For harvesting reasons, the defoliation of green leaf parts compared to a pure desiccation and wilting of the rest

Plant preferred in order to avoid a strong reduction in fiber quality due to contamination - caused by withered leaf residues.

The defoliantia used up to now leave much to be desired compared to essential requirements such as quick and lasting effectiveness even in cool temperature conditions, low application rates, low environmental impact (toxicity, smell, flammability). The object of the invention was therefore to provide better compounds which are used for the removal, in particular for the targeted induction of the dropping of leaves, flowers or

Fruits in crops such as cotton, citrus, olives and pome and stone fruit and / or as desiccants for drying up the aerial parts in crops (e.g. potato, rapeseed, sunflower and soybean) can be used.

We have found that this object is achieved by the 3-phenylurazil derivatives defined at the outset, which are superior to the known abscess and

Desiccants have advantages. With regard to the use of the compounds I for the desiccation and abscess of plant organs, preference is given to those in which the variables have the following meaning: R ^{1 is} a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, the formyl group, a C ₂ -C ₆ alkanoyl group, a C ₃ -C ₄ alkenyl group or a C ₃ -C ₄ alkynyl group, very particularly preferably methyl;

- a C ₁ -C ₈ alkoxy group, a C ₃ -C ₇ cycloalkoxy group, a C ₃ -C ₈ alkenyloxy group, a C ₃ -C ₆ alkynyloxy group, - a C ₁ -C ₈ haloalkoxy group, a C ₃ -C ₉ haloalkenyloxy group, a C ₃ -C ₈ haloalkynyloxy group, - a cyano-C ₁ -C ₈ alkoxy group, preferably a group

H / alkyl

I.

-O- (C) _1-5 -CN

I.

H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 8; - A Νitro-C ₁ -C ₈ alkoxy group, preferably a group

H / alkyl

I.

-O- (C) _1-5 -ΝO ₂

H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 1 to 8;

a C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkoxy group, a

C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxy group such as methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, (1-methylethoxy) methoxy, n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, ( 1,1-dimethylethoxy) methoxy, methoxyethoxy, ethoxyethoxy, n-propoxyethoxy, (1-methylethoxy) ethoxy, n-butoxyethoxy,

(1-methylpropoxy) ethoxy, (2-methylpropoxy) ethoxy, (1,1-di- methylethoxy) ethoxy, 3- (methoxy) propoxy, 2- (methoxy) propoxy and 2- (ethoxy) propoxy, preferably methoxymethoxy and

Ethoxymethoxy, - a C ₅ -C ₇ cycloalkoxy-C ₁ -C ₄ alkoxy group, a

C ₃ -C ₈ alkenyloxy-C ₁ -C ₄ alkoxy group, a

C ₃ -C ₈ alkynyloxy-C ₁ -C ₄ alkoxy group, - a C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxy group, - a di- (C ₁ - C ₄ alkoxy) -C ₁ -C ₄ alkoxy group, preferably a group

H / alkyl H / alkyl

I I

-O- (C) _1-3 CO alkyl

| |

H / alkyl alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 4 to 9; a C ₁ -C ₄ haloalkoxy-C ₁ -C ₄ alkoxy group, a

C ₃ -C ₄ haloalkenyloxy-C ₁ -C ₄ alkoxy group, - a C ₁ -C ₄ alkylthio-C ₁ -C ₄ alkoxy group, a C ₅ -C ₇ cycloalkylthio-C ₁ -C ₄ alkoxy group, a C ₃ -C ₆ alkenylthio-C ₁ -C ₄ alkoxy group,

a C ₃ -C ₆ -alkynylthio-C ₁ -C ₄ -alkoxy group, - a C ₁ -C ₄ -alkoxy-C ₃ -C ₆ -alkenyloxy group, a C ₁ -C ₄ -alkylthio-C ₃ - C ₆ -alkenyloxy group, a C ₁ -C ₄ -alkoxy-C ₃ -C ₆ -alkynyloxy group, a C ₁ -C ₄ -alkylthio-C ₃ -C ₆ -alkynyloxy group, - a C ₁ -C ₄ -alkylsulfinyl -C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylsulfonyl-C ₁ -C ₄ alkoxy group, a formyl C ₁ -C ₄ alkoxy group or an alkylcarbonyl-C ₁ -C ₄ - alkoxy group, preferably a group

H / alkyl

I.

-O- (C) _1-4 -CO-H / alkyl

|

H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 8; a C ₂ -C ₅ alkoxycarbonyl-C ₁ -C ₄ alkoxy group,

- A tri- (C ₁ -C ₄ alkyl) silyl-C ₁ -C ₄ alkoxy group, in particular a group

H / alkyl

I.

-O- (C) _1-3 -Si (alkyl) ₃

|

H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 4 to 8; - a C ₂ -C ₈ alkylidene aminooxy-C ₁ -C ₄ alkoxy group, especially a group

H / alkyl H / alkyl

| H / alkyl |

-O- (C) _1-2 -ON = or -O- (C) _1-2 -ON = CH ₂ ) ₂ -6

I

H / alkyl I.

H / alkyl H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 3 to 9; a C ₁ -C ₄ alkoxy group which is substituted by hydroxyl, formyl,

C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ haloalkylcarbonyl or

C ₂ -C ₅ alkoxycarbonyl is substituted, in particular an H / alkyl group

I.

-O- (C) 2 _2-5 -O- (H / COH / CO-alkyl / CO-haloalkyl / CO-O-alkyl)

|

H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 3 to 10;

a C ₁ -C ₄ alkoxy group which is represented by P (= O) (C ₁ -C ₄ alkyl) ₂ ,

P (= O) (C ₁ -C ₄ alkoxy) ₂ , P (= O) (C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy),

P (= S) (C ₁ -C ₄ alkyl) ₂ . P (= S) (C ₁ -C ₄ alkoxy) ₂ or P (= S) (C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy) is substituted, especially a group

H / alkyl H / alkyl

| Alkyl / alkoxy | Alkyl / alkoxy

-O- (C) _1-3 - or -O- (C) _1-3 - |

Alkyl / alkoxy I alkyl / alkoxy

H / alkyl H / alkyl in which the alkyl and / or alkoxy radicals can be the same or different and the sum of the C atoms is 3 to 8; a carbamoyl-C ₁ -C ₄ -alkoxy group, the nitrogen atom of which carries one or two C ₁ -C ₄ -alkyl radicals if desired or the nitrogen atom of which can be part of a 3- to 7-membered azaheterocyclic ring, in particular a group

H / alkyl H / alkyl

| H / alkyl |

-O- (C) _1-5 -O- or -O- (C) _1-2 -O- CH ₂ ) ₂ -6

|

H / alkyl |

H / alkyl H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 10; a β-aminoethoxy group, the nitrogen atom being a C ₁ -C ₄ -alkyl radical and, if desired, a further one

C ₁ -C ₄ alkyl, formyl, C ₂ -C ₅ alkylcarbonyl or C ₂ -C ₅ alkoxycarbonyl radical or may be part of a 3- to 7-membered azaheterocyclic ring, in particular one

group

H / alkyl

-O-CH ₂ CH ₂ - or -O-CH ₂ CH ₂ - CH ₂ ) ₂ -

(H / alkyl / COH / CO-alkyl / CO-O-alkyl)

in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 8; a phenyl-C ₁ -C ₄ -alkoxy group, a phenoxy-C ₁ -C ₄ -alkoxy group, a phenoxy-C ₃ -C ₄ -alkynyloxy group, a benzyloxy-C ₁ -C ₄ -alkoxy group, a phenylthio-C ₁ - C ₄ -alkoxy group, a phenylsulfinyl-C ₁ -C ₄ -alkoxy group or a phenylsulfonyl-C ₁ -C ₄ -alkoxy group, the phenyl ring of each of these groups optionally having one to three substituents can be selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ haloalkoxy, hydroxyl, hydroxycarbonyl and C ₂ -C ₅ alkoxycarbonyl;

- A benzoyl-C ₁ -C ₄ alkoxy group, especially a group

H / alkyl

I.

-O- (C) _1-4 -CO- (unsubstituted or substituted phenyl),

I.

H / alkyl in which the alkyl radicals can be the same or different and the sum of the carbon atoms in the alkoxy part is 2 to 8, the phenyl ring optionally being able to carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy, hydroxyl, hydroxycarbonyl and C ₂ -C ₅ - Alkoxycarbonyl;

- A saturated or partially or completely unsaturated 3- to 7-membered heterocyclyloxy, heterocyclyl-C ₁ -C ₄ alkoxy or heterocyclyloxy-C ₁ -C ₄ alkoxy group, in particular a group

-O- (CH ₂ ) _0-3 - (unsubstituted or substituted

Heterocyclyl) or

-O- (CH ₂ ) _0-3 -O (unsubstituted or substituted

Heterocyclyl) where the heterocycle can each carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and the heterocycle can also carry one of the following radicals on each substitutable ring member: cyano, nitro , Halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy;

- The formyloxy group, a C ₂ -C ₈ alkylcarbonyloxy group, a C ₄ -C ₈ cycloalkylcarbonyloxy group, a C ₃ -C ₈ alkenylcarbonyloxy group, a C ₃ -C ₈ alkynylcarbonyloxy group, a

Cyano-C ₃ -C ₆ alkylcarbonyloxy group, a C ₂ -C ₈ haloalkylcarbonyloxy group, a C ₃ -C ₆ cycloalkyl-C ₂ -C ₅ alkylcarbonyloxy group, a C ₁ -C ₄ alkoxy-C ₂ -C ₅ -alkylcarbonyloxy group, a C ₂ -C ₅ alkylcarbonyl-C ₂ -C ₅ alkylcarbonyloxy group, in particular a group

H / alkyl

I.

-O-CO- (C) _1-3 -CO-alkyl

I.

H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 4 to 9, a C ₂ -C ₈ alkoxycarbonyloxy group such as methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy , 1-methyl-propoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy , 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbon , 3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy, 2-ethylbutoxycarbonyloxy, 1,1,2-trimethylpropoxycarbonyloxy,

1,2,2-trimethylpropoxycarbonyloxy, 1-ethyl-1-methylpropoxycarbonyloxy, l-ethyl-2-methylpropoxycarbonyloxy and n-heptoxycarbonyloxy, a C ₆ -C ₈ cycloalkoxycarbonyloxy group such as cyclohexoxycarbonyloxy, cycloheptoxycarbonyloxy and cyclooctoxycarbonyloxy, a C ₃ -C _8- alkenyloxycarbonyloxy group such as prop-2-enyloxycarbonyloxy, but-2-enyloxycarbonyloxy, but-3-enyloxycarbonyloxy, 1-methyl-prop-2-enyloxycarbonyloxy, 2-methyl-prop-2-enyloxycarbonyloxy, pent-2-enyloxycarbonyloxy, Pent-3-enyloxycarbonyloxy, pent-4-enyloxycarbonyloxy, 1-methyl-but-2-enyl-oxycarbonyloxy, 2-methyl-but-2-enyloxycarbonyloxy, 3-methyl-but-2-enyloxycarbonyloxy, 1-methyl but-3-enyloxycarbonyloxy, 2-methyl-but-3-enyloxycarbonyloxy, 3-methyl-but-3-enyloxycarbonyloxy, 1,1-dimethyl-prop-2-enyloxycarbonyloxy, 1,2-dimethyl-prop-2- enyloxycarbonyloxy, 1-ethyl-prop-2-enyloxycarbonyloxy, hex-2-enyloxycarbonyloxy, hex-3-enyloxycarbonyloxy, hex-4-enyloxycarbonyloxy, hex-5-enyloxycarbonyloxy, 1-methyl-2-pentenyloxycarbonyloxy, 2-methyl-pent-2-enyl-oxycarbonyloxy, 3-methyl-pent-2-enyloxycarbonyloxy, 4-methylpent-2-enyloxycarbonyloxy, 1-methyl-pent-3-enyloxycarbonyloxy, 2- Methyl-pent-3-enyloxycarbonyloxy, 3-methyl-pent-3-enyloxycarbonyloxy, 4-methyl-pent-3-enyloxycarbonyloxy,

1-methyl-pent-4-enyloxycarbonyloxy, 2-methyl-pent-4-enyloxycarbonyloxy, 3-methyl-pent-4-enyloxycarbonyloxy, 4-methylpent-4-enyloxycarbonyloxy, 1,1-dimethyl-but-2-enyloxycarbonyloxy, 1,1-dimethyl-but-3-enyloxycarbonyloxy, 1,2-dimethyl-but-2-enyloxycarbonyloxy, 1,2-dimethyl-but-3-enyloxycarbonyloxy, 1,3-dirnethyl-but-2-enyloxycarbonyloxy, 1, 3-dimethyl-but-3-enyloxycarbonyloxy, 2,2-dimethyl-but-3-enyloxycarbonyloxy, 2,3-dimethyl-but-2-enyloxycarbonyloxy, 2, 3-dimethyl-but-3-enyloxycarbonyloxy, 3,3- Dimethyl-but-2-enyloxycarbonyloxy, 1-ethyl-but-2-enyl, 1-ethyl-but-3-enyloxycarbonyloxy, 2-ethyl-but-2-enyloxycarbonyloxy, 2-ethyl-but-3- enyloxycarbonyloxy, 1,1,2-trimethyl-prop-2-enyloxycarbonyloxy, 1-ethyl-1-methyl-prop-2-enyloxycarbonyloxy and 1-ethyl-2-methyl-prop-2-enyloxycarbonyloxy; a C ₄ -C ₈ alkynyloxycarbonyloxy group such as prop-2-ynyloxycarbonyloxy, but-2-ynyloxycarbonyloxy, but-3-ynyloxycarbonyloxy, 1-methyl-prop-2-ynyloxycarbonyloxy, pent-2-ynyloxycarbonyloxy, pent-3-ynyloxycarbonyloxy, pent -4-inyloxycarbonyloxy, 1-methyl-but-2-inyloxycarbonyloxy, 1-methyl-but-3-inyloxycarbonyloxy, 2-methyl-but-3-inyloxycarbonyloxy, 1,1-dimethylprop-2-inyloxycarbonyloxy, 1-ethyl-prop -2-inyl-oxycarbonyloxy, hex-2-inyloxycarbonyloxy, hex-3-inyloxycarbonyloxy, hex-4-inyloxycarbonyloxy, hex-5-inyloxycarbonyloxy, 1-methylpent-2-inyloxycarbonyloxy, 1-methylpent-3-inyloxycarbonyloxy , 1-methylpent-4-ynyloxycarbonyloxy, 2-methylpent-3-ynyloxycarbonyloxy, 2-methylpent-4-ynyloxycarbonyloxy, 3-methylpent-4-ynyloxycarbonyloxy, 4-methylpent-2-ynyloxycarbonyloxy, 1 , 1-dimethyl-but-2-ynyloxycarbonyloxy, 1,1-dimethyl-but-3-ynyloxycarbonyloxy, 1,2-dimethyl-but-3-ynyloxycarbonyloxy, 2,2-dimethyl-but-3-ynyloxycarbonyloxy, 1-ethylbut -2-inyloxycarbonyloxy, 1-ethyl-but-3-inyloxycarbonylox y, 2-ethyl-but-3-ynyloxycarbonyloxy and 1-ethyl-1-methylprop-2-ynyloxycarbonyloxy; a C ₂ -C ₈ haloalkoxycarbonyloxy group, a C ₃ -C ₆ cycloalkyl-C ₂ -C ₅ alkoxycarbonyloxy group, a C ₁ -C ₄ alkoxy-C ₂ -C ₅ alkoxycarbonyloxy group, a C ₁ -C ₄ alkyl (thiocarbonyl) oxy group, a C ₁ -C ₄ alkyl thiocarbonyloxy group, a C ₁ -C ₆ alkoxy (thiocarbonyl) oxy group, a C ₁ -C ₆ alkyl thio ( thiocarbonyl) oxy group, the carbamoyloxy group which can carry one of the following radicals: C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, phenyl or phenyl-C ₁ -C ₄ alkyl, where the phenyl rings in turn can carry one to three substituents selected from a group consisting of cyano, nitro, Halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and

C ₁ -C ₄ haloalkoxy; - an N, N-di (C ₁ -C ₄ alkyl) carbamoyloxy group, an N, N-di (C ₃ -C ₄ alkenyl) carbamoyloxy group, a

N- (C ₁ -C ₄ alkyl) -N- (C ₃ -C ₄ alkenyl) carbamoyloxy group,

- the aziridinyl-carbonyloxy, azetanyl-carbonyloxy,

Pyrrolidinylcarbonyloxy, piperidinyl-carbonyloxy or azepanyl-carbonyloxy group,

- An N- (C ₁ -C ₄ alkyl) thiocarbamoyloxy or N, N- di (C ₁ -C ₄ alkyl) thiocarbamoyloxy group, in particular a group

H / alkyl

-O-CS

Alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 9, - the benzoyloxy or phenoxycarbonyloxy group, one

Phenyl (C ₁ -C ₄ alkyl) carbonyloxy or phenyl (C ₁ -C ₄ alkoxy) carbonyloxy group, the phenyl rings of these four groups optionally being able to carry one to three substituents, selected from a group consisting of Cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl,

C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy; a C ₂ -C ₅ alkylcarbonyloxy group such as methylcarbonyloxy,

Ethylcarbonyloxy, n-propylcarbonyloxy, 1-methyl-ethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy,

2-methylpropylcarbonyloxy and 1,1-dimethylethylcarbonyloxy, which are substituted by hydroxyl, formyloxy, alkylcarbonyloxy, alkoxy carbonyloxy, carbamoyloxy, N-alkylcarbamoyloxy, N, N-dialkylcarbamoyloxy, aziridin-1-ylcarbonyloxy, azetan-1-ylcarbonyloxy, pyrrolidin-1-yl-carbonyloxy, piperidin-1-yl-carbonyloxy, azepan-1-yl-carbonyloxy, Hydroxycarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, carbamoyl, N-alkyIcarbamoyl, N, N-

DialkyIcarbamoyl, Aziridin-1-ylcarbonyl, Azetan-1-ylcarbonyl, Pyrrolidin-1-yl-carbonyl, Piperidin-1-yl-carbonyl or

Azepan-1-yl-carbonyl, can be substituted with the proviso that the sum of the carbon atoms is 2 to 10, in particular one group

H / alkyl

-O-CO- (C) _1-5 -O- (H / CHO / CO-alkyl / CO-haloalkyl / CO-O-alkyl),

H / alkyl

H / alkyl H / alkyl

H / alkyl

-O-CO- (C) _1-5 -O-CO- or -O-CO- (C) _1-5 -O-CO- _2-6 ,

H / alkyl

H / alkyl H / alkyl H / alkyl H / alkyl

H / alkyl

-O-CO- (C) _0-5 -CO-N or -O-CO- (C) _0-5 -O-CO-) _2-6 .

IH / alkyl

H / alkyl H / alkyl

where the alkyl groups can in each case be the same or different and the sum of the C atoms is 2 to 10, a saturated or partially or completely unsaturated 3- to 7-membered heterocyclylcarbonyloxy or heterocyclic-C ₁ -C ₄ -alkylcarbonyloxy group, where the heterocycles can carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and the heterocycles can carry one of the following radicals on each substitutable carbon atom: cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and

C ₁ -C ₄ haloalkoxy, - A C ₁ -C ₈ alkylsulfonyloxy or C ₁ -C ₅ alkoxysulfonyloxy group, - the sulfamoyloxy group, the nitrogen atom of which carries two of the following radicals: hydrogen, C ₁ -C ₄ alkyl and / or

C ₃ -C ₆ cycloalkyl; - the aziridin-1-ylsulfonyloxy-, azetan-1-ylsulfonyloxy-,

Pyrrolidin-1-yl-sulfonyloxy, piperidin-1-yl-sulfonyloxy or azepan-1-yl-sulfonyloxy group - the phenylsulfonyloxy or phenyl-C ₁ -C ₄ -alkylsulfonyloxy group, the phenyl rings of these groups being optionally one to three Can carry substituents selected from a group consisting of cyano, nitro, halogen,

C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy;

R ² particularly preferably means:

- C ₁ -C ₈ alkoxy, preferably C ₁ -C ₃ alkoxy;

- C ₃ -C ₇ cycloalkoxy such as cyclopropoxy, cyclopentoxy and cyclohexoxy;

- C ₃ -C ₆ alkenyloxy, preferably allyloxy;

- C ₃ -C ₆ alkynyloxy, preferably propargyloxy; - C ₃ -C ₇ cycloalkyl-C ₁ -C ₂ alkoxy such as cyclopropoxymethyl, cyclopentoxymethyl, cyclohexoxymethyl, 2- (cyclopropoxy) ethyl, 2- (cyclopentoxy) ethyl and 2- (cyclohexoxy) ethyl ;

Phenyl-C ₁ -C ₄ -alkoxy or phenoxy-C ₁ -C ₄ -alkoxy such as benzyloxy, 1-phenylethyloxy, 2-phenylethyloxy, 1-phenylprop-l-yloxy,

2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 2-phenylbut-1-yloxy, 3-phenylbut-l-yloxy, 4-phenylbut-1- yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy,

3-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy, 1- (phenylmethyl) eth-1-yloxy, 1- (phenylmethyl) -1- (methyl ) -eth-1-yloxy, phenoxymethoxy, 1- (phenoxy) ethyloxy, 2- (phenoxy) ethyloxy, 1- (phenoxy) prop-1-yloxy, 2- (phenoxy) prop-1-yloxy, 3- (Phenoxy) prop-1-yloxy, 1- (phenoxy) but-1-yloxy, 2- (phenoxy) but-1-yloxy, 3- (phenoxy) but-1-yloxy, 4- (phenoxy) but -1-yloxy, 1- (phenoxy) but-2-yloxy, 2- (phenoxy) but-2-yloxy, 3- (phenoxy) but-2-yloxy, 3- (phenoxy) but-2-yloxy , 4- (phenoxy) but-2-yloxy, 1- (phenoxymethyl) eth-1-yloxy and 1- (phenoxymethyl) -1- (methyl) -eth-1-yloxy, preferably benzyloxy,

where the phenyl rings can each carry one to three substituents selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl,

C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio;

- C ₁ -C ₈ haloalkoxy, preferably C ₁ -C ₄ haloalkoxy; - C ₃ -C ₉ haloalkenyloxy, preferably C ₃ -C ₆ haloalkenyloxy;

C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxy such as methoxymethyl, ethoxymethyl, n-propoxymethyl, (1-methylethoxy) methyl, n-butoxymethyl,

(1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1,1-dimethylethoxy) methyl, methoxyethyl, ethoxyethyl, n-propoxyethyl, (1-methylethoxy) ethyl, n-butoxyethyl, (1-methylpropoxy) ethyl, (2-methylpropoxy) ethyl, (1,1-dimethylethoxy) ethyl, 3- (methoxy) propyl, 2- (methoxy) propyl and

2- (ethoxy) propyl;

- C ₃ -C ₆ haloalkenyloxy-C ₁ -C ₂ alkoxy; - C ₁ -C ₄ -Alkylthio-C ₁ -C ₄ -alkoxy such as methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, (1-methylethylthio) methyl, n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl , (1,1-dimethylethylthio) methyl, methylthioethyl, ethylthioethyl, n-propylthioethyl, (1-methylethylthio) ethyl, n-butylthioethyl, (1-methylpropylthio) ethyl, (2-methylpropylthio) ethyl, (1,1-dimethylethylthio) ethyl, 3- (methylthio) propyl, 2- (methylthio) propyl and 2- (ethylthio) propyl; - N N-alkyl- or N, N-dialkylcarbamoylalkoxy, the sum of the C atoms being 2 to 10; - C ₁ -C ₈ alkylsulfonyloxy, preferably C ₁ -C ₄ alkylsulfonyloxy;

Phenylsulfonyloxy, which can also carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ - C ₄ alkylthio;

- N-alkyl- or N, N-dialkylsulfamoyloxy, in which the sum of the carbon atoms is 1 to 8; R ³

Halogen, especially chlorine or bromine; R ⁴

Hydrogen and fluorine;

R ₅

Hydrogen, fluorine, chlorine or methyl;

R ⁶

Methyl or trifluoromethyl; R ⁷ , R ⁸ - hydrogen, - a C ₁ -C ₈ alkyl radical which can also carry one of the following substituents: cyano, nitro, hydroxyl, hydroxycarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio , C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkoxycarbonyl, C ₁ -C ₄ alkylsulfonyl or di- (C ₁ -C ₄ alkyl) -phosphono; - A C ₂ -C ₈ -alkenyl radical, a C ₃ -C ₈ -alkynyl radical, one

C ₁ -C ₈ haloalkyl, a C ₃ -C ₈ cycloalkyl, a C ₁ -C ₈ alkoxy; the phenyl radical or a phenyl-C ₁ -C ₄ -alkyl radical, where in each case a saturated five- to seven-membered ring with optionally 1 or 2 oxygen atoms as ring members can be fused to the phenyl ring, for example 1,3-benzodioxolan-5-yl and 1,3-benzodioxan-6-yl,

and wherein the phenyl rings in turn can carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy, hydroxyl,

Hydroxycarbonyl

and C ₂ -C ₅ alkoxycarbonyl; with the proviso that R ⁷ and R ⁸ do not both simultaneously represent a C ₁ -C ₈ alkoxy radical, or

R ⁷ and R ⁸ together with the common nitrogen atom form a four to seven-membered heterocyclic ring which can also carry one to three C ₁ -C ₆ -alkyl groups, one of the ring members being -O-, -S-, -N =, -NH - or -N (C ₁ -C ₄ alkyl) - can be substituted, for example pyrrolidinyl, piperidinyl, hexahydroazepinyl, morpholinyl, thiomorpholinyl, piperazinyl and 4-methyl-piperazinyl; R ^{9 is} a radical -OC (R ¹⁰ , R ¹¹ ) -CH ₂ -ON = C (R ¹² , R ¹³ ),

-O-CH ₂ -ON = C (R ¹² , R ¹³ ), -ON = C (R ¹⁴ , R ¹⁵ ), -OR ¹⁶ or -SR ¹⁷ where R ^{3 is} not -OC (R ¹⁰ , R ¹¹ ) - CH ₂ -ON = C (R ¹² , R ¹³ ), -O-CH ₂ -ON = C (R ¹² , R ¹³ ) or -ON = C (R ¹⁴ , R ¹⁵ ), if

R ^{1 represents} hydrogen; R ^{10 represents} hydrogen or C ₁ -C ₄ alkyl,

R ¹¹ denotes hydrogen, C ₁ -C ₄ alkyl, phenyl or benzyl,

R ^{12 represents} hydrogen or C ₁ -C ₆ alkyl,

R ^{13 represents} C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl or phenyl, or R ¹² and R ¹³ together represent a three- to six-membered group

Alkylene chain,

R ^{14 represents} C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylthio, C ₂ -C ₇ alkoxycarbonyl or C ₂ -C ₇ alkoxycarbonyl-C ₁ -C ₄ alkyl;

R ¹⁵ denotes C ₁ -C ₆ alkyl, trifluoromethyl, C ₃ -C ₆ cycloalkyl,

R ^{1 (S} means C ₁ -C ₈ haloalkyl, C ₃ -C ₅ haloalkenyl or

C ₃ -C ₅ haloalkynyl or - [C (R ¹⁸ , R ¹⁹ )] _m -Q, where the substituents

R ¹⁸ and R ^{19 are} independently hydrogen or

C ₁ -C ₃ alkyl, m stands for 0.1 or 2 and

Q stands for

C ₃ -C ₇ cycloalkyl which can also carry a C ₁ -C ₄ alkyl group on each substitutable C atom, preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; a saturated three- to seven-membered heterocycle with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms and

if desired, a carbonyl group as a ring member, the heterocycle at each substitutable carbon atom

C ₁ -C ₄ alkyl group, preferably oxiran-2-yl, 2-methyl-oxiran-2-yl, oxetan-3-yl, 3-methyl-oxetan-3-yl, 3-ethyl-oxetan-3 -yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 3-methylthietan-3-yl, tetrahydrothien-3-yl, 1 , 3-dioxolan-5-yl, 1,3-dioxan-5-yl or 1-oxotetrahydrothiopyran-4-yl, or

Phenyl, which can optionally carry one to three radicals, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and

C ₁ -C ₄ alkylthio, and where the phenyl ring can also carry a fused-on five- to seven-membered carbocyclic ring or a fused-on heterocyclic ring with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms, preferably phenyl, 1 , 3-benzodioxol-5-yl or 1,3-benzodioxan-6-yl;

and

R ¹⁷ denotes hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ alkenyl,

C ₃ -C ₈ alkynyl, C ₂ -C ₆ alkoxyalkyl, C ₃ -C ₈ cycloalkyl, which, if desired, can also carry one to 3 C ₁ -C ₄ alkyl groups, phenyl or benzyl; as well as the enol ethers of those compounds I in which R ¹ denotes a C ₁ -C ₄ alkyl, C ₂ -C ₅ alkenyl or C ₃ -C ₅ alkynyl group, unless R ² denotes a group above -O -SO ₂ - bound group or a group -CO-O-CH ₂ -CH ₂ -ON = C (R ¹² , R ¹³ ) with R ¹² and R ¹³ C ₁ -C ₄ alkyl.

The meanings given for the substituents R ¹ to R ¹⁷ are collective terms for individual lists of the individual group members. All alkyl, alkenyl, alkynyl, haloalkyl and haloalkoxy parts can be straight-chain or branched. The haloalkyl and haloalkoxy radicals can carry the same or different halogen atoms.

Specifically, for example: halogen: fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine; - C ₁ - _C4 alkyl and C ₁ -C ₄ alkyl parts in larger residues: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,

2-methylpropyl and 1,1-dimethylethyl, - C ₁ -C ₄ haloalkyl and C ₁ -C ₄ haloalkyl parts in larger residues: chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1- Fluoroethyl,

2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,

2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

- C ₃ -C ₆ alkenyl and C ₃ -C ₆ alkenyl parts in larger residues:

Prop-2-enyl, but-2-enyl, but-3-enyl, 1-methyl-prop-2-enyl, 2-methyl-prop-2-enyl, pent-2-enyl, pent-3-enyl, Pent-4-enyl, 1-methyl-but-2-enyl, 2-methyl-but-2-enyl, 3-methyl-but-2-enyl, 1-methyl-but-3-enyl, 2-methyl but-3-enyl,

3-methyl-but-3-enyl, 1,1-dimethyl-prop-2-enyl, 1,2-dimethyl-prop-2-enyl, 1-ethyl-prop-2-enyl, hex-2-enyl, Hex-3-enyl, hex-4-enyl, hex-5-enyl, 1-methyl-2-pentenyl, 2-methyl-pent-2-enyl, 3-methyl-pent-2-enyl, 4-methyl pent-2-enyl, 1-methyl-pent-3-enyl, 2-methyl-pent-3-enyl, 3-methyl-pent-3-enyl, 4-methyl-pent-3-enyl, 1-methyl pent-4-enyl, 2-methyl-pent-4-enyl, 3-methyl-pent-4-enyl, 4-methyl-pent-4-enyl, 1,1-dimethyl-but-2-enyl, 1, 1-dimethyl-but-3-enyl, 1,2-dimethyl-but-2-enyl, 1,2-dimethyl-but-3-enyl, 1,3-dimethyl-but-2-enyl, 1, 3-dimethyl-but-3-enyl, 2,2-dimethyl-but-3-enyl, 2, 3-dimethyl-but-2-enyl, 2,3-dimethyl-but-3-enyl, 3, 3-dimethyl-but-2-enyl, 1-ethyl-but-2-enyl, 1-ethyl-but-3enyl, 2-ethyl-but-2-enyl, 2-ethyl-but-3-enyl, 1, 1,2-trimethyl-prop-2-enyl, 1-ethyl-1-methyl-prop-2-enyl and 1-ethyl-2-methyl-prop-2-enyl;

- C ₃ -C ₆ alkynyl and C ₃ -C ₆ alkynyl parts in larger residues:

Prop-2-ynyl, but-2-ynyl, but-3-ynyl, 1-methyl-prop-2-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, l-methyl- but-2-ynyl, 1-methyl-but-3-ynyl, 2-methyl-but-3-ynyl, 1,1-dimethyl-prop-2-ynyl, 1-ethyl-prop-2-ynyl, hex 2-inyl, hex-3-inyl, hex-4-inyl, hex-5-inyl, 1-methyl-pent-2-inyl, 1-methyl-pent-3-inyl, 1-methyl-pent-4- inyl, 2-methyl-pent-3-inyl, 2-methyl-pent-4-inyl, 3-methyl-pent-4-inyl, 4-methyl-pent-2-inyl, 1,1-dimethyl-but- 2-inyl, 1,1-dimethyl-but-3-ynyl, 1,2-dimethyl-but-3-ynyl, 2,2-dimethyl-but-3-ynyl,

1-ethyl-but-2-ynyl, 1-ethyl-but-3-ynyl, 2-ethyl-but-3-ynyl and 1-ethyl-1-methyl-prop-2-ynyl; C ₃ -C ₆ haloalkenyl and C ₃ -C ₆ haloalkenyl parts in larger residues:

2-chloroprop-2-enyl, 3-chloroprop-2-enyl, 2,3-dichloroprop-2-enyl, 3,3-dichloroprop-2-enyl, 2,3,3-trichloroprop-2- enyl, 2,3-dichlorobut-2-enyl, 2-bromoprop-2-enyl,

3-bromoprop-2-enyl, 2,3-dibromoprop-2-enyl, 3,3-dibromoprop-2-enyl, 2,3,3-tribromoprop-2-enyl and 2,3-dibromobut- 2-enyl; C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkoxy parts in larger residues: methoxy, ethoxy, n-propyloxy, 1-methylethoxy, n-butyloxy,

1-methyl-propyloxy, 2-methylpropyloxy and 1, 1-dimethylethoxy; C ₁ -C ₄ alkylthio and C ₁ -C ₄ alkylthio parts in larger residues: methylthio, ethylthio, n-propylthio, 1-methyl-ethylthio, n-butylthio, 1-methyl-propylthio, 2-methyl-propylthio and

1, 1-dimethylethylthio; C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkoxy parts in larger residues: chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-fluoroethoxy, 2,2-fluoroethoxy, 2,2-fluoroethoxy -Difluoroethoxy, 2,2,2-trifluoroethoxy,

2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy;

C ₂ -C ₅ alkoxycarbonyl and C ₂ -C ₅ alkoxycarbonyl parts in larger residues: methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, 1-methyl-ethoxycarbonyl, n-butoxycarbonyl, 1-methylpropyloxycarbonyl, 2-methylpropyloxycarbonyl, and 1, 1-dimethylethoxycarbonyl; C ₁ -C ₄ alkylsulfonyl: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;

C ₃ -C ₈ cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;

Phenyl-C ₁ -C ₄ -alkyl: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1- yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl,

4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl,

3-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-2l, 1- (phenylmethyl) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-1-yl and 1- (phenylmethyl) prop-1-yl.

Examples of 3- to 7-membered heterocyclyl radicals are oxiranyl, furan-2-yl, tetrahydrofuran-2-yl, 1,3-dioxolan-2-yl, 1,3-oxathiolan-2-yl, 1,3-dithiolane 2-yl, tetrahydro-2H-pyran-2-yl, 2-oxotetra-hydrofuran-2-yl, thien-2-yl, pyridin-2-yl, pyridin-3-yl, pyrimidin-2-yl and 1-methyl-3-trifluoromethyl-1H-1,3,4-triazol-5-yl.

The following combinations of the meanings of R ¹ to R ⁶ are very particularly preferred:

R ^{1 is} a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, the formyl group, a C ₂ -C ₆ alkylcarbonyl group, a

C ₃ -C ₄ alkenyl group or a C ₃ -C ₄ alkynyl group, in particular methyl;

R ³ halogen or cyano, especially chlorine;

R ^{4 is} hydrogen or halogen, especially fluorine;

R ^{5 is} hydrogen and R ^{6 is} a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group, in particular trifluoromethyl.

For example, the following urazil derivatives are listed: 3- (4-chloro-2-fluoro-5-isopropoxyphenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (No. 1), mp. 85-90 ° C;

3- (4-chloro-2-fluoro-5-isopropoxyphenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (No. 2), mp 195-196 ° C;

3- (4-chloro-2-fluoro-5-propargyloxyphenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (No. 3), mp 127-128 ° C;

3- (4-chloro-2-fluoro-5-propargyloxyphenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (No. 4), mp 130-136 ° C;

3- (4-chloro-3-diethylaminocarbonylphenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione (No. 5), oil; 3- [4-Chloro-3- (2- (prop-2-yl-iminooxy) ethoxycarbonyl) phenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione (No. 6 ), Mp 84-86 ° C; 3- [4-chloro-3- (tetrahydro- (2H) pyran-3-yl) methoxycarbonyl) phenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione (No. 7), oil;

3- [4-Chloro-3 - ((methoxy) methylaminocarbonyl) phenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione (No. 8), mp.

118-120 ° C;

3- [4-chloro-3-alkylaminocarbonylphenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione (No. 9).

Suitable salts of the compounds I which can be used in agriculture are in general the salts of those bases which do not impair the defoliation activity of I. Particularly suitable as basic salts are those of the alkali metals, preferably the sodium and potassium salts, those of the alkaline earth metals, preferably calcium, magnesium and barium salts and those of the transition metals, preferably manganese, copper, zinc and iron salts and the ammonium salts can carry up to three C ₁ -C ₄ alkyl, hydroxy-C ₁ -C ₄ alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium,

Trimethylbenzylammonium and trimethyl- (2-hydroxyethyl) ammonium salts, the phosphonium salts, the sulfonium salts, preferably tri- (C ₁ -C ₄₎ alkylsufoniumsalze, and (C ₁ -C ₄₎ alkylsulfoxoniumsalze the sulfoxonium salts, preferably tri-.

The 3-phenylurazil derivatives I are known or can be prepared by known methods, such as can be found in the following published documents: EP-A 255 047,

EP-A 260 621, WO 88/10254, WO 89/02891, WO 89/03825, WO 91/07392 and WO 91/07393.

If R ^{1 is} hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₅ alkenyl or

C ₃ -C ₅ alkynyl, the 3-phenylurazil derivatives I can also be written in the tautomeric formulas Ia or Ib [-NH-CO- <---> -N = C (OH) -] as enol ethers:

Compounds of formula I '

in the R ¹ 'C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl and R ² ' a group bonded via -O-, -O-CO-, -O-CS- or -O-SO ₂ - , in particular one of the preferred groups mentioned for R ^{2 in} this regard, are new. They can be prepared from the known 3-phenylurazil derivatives I, where R ^{1 is} hydrogen, by alkylation with a suitable alkylating agent (cf., for example, Houben-Weyl, Methods of Organic Chemistry, Vol. E5 / 2, p. 998 ff) .

Particularly suitable alkylating agents are alkenyls or alkynyls with a leaving group L, where L represents a halide, preferably chloride or bromide, a sulfate, trifluoroacetate, mesylate, tosylate residue or a hydroxyl residue. The alkylation is advantageously carried out in the presence of an inert, organic solvent at a reaction temperature between 0 and approximately 100 ° C., preferably between 0 and 40 ° C.

In particular, aprotic solvents, for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or aliphatic ketones such as acetone, or aprotic, polar solvents such as dimethylformamide and dimethyl sulfoxide, are used as solvents. but also protic solvents, for example lower alcohols such as ethanol, optionally in a mixture with water. Depending on the starting materials and the solvent, the reaction in the presence of a base and optionally a catalyst can be advantageous. Suitable bases for this are, for example, alkali metal hydrides such as

Sodium and potassium hydride, alkali metal alcoholates such as sodium methoxide and potassium tert. -butanolate, alkali metal hydroxides such as sodium and potassium hydroxide or basic metal salts such as potassium carbonate, sodium carbonate and sodium hydrogen carbonate.

The starting products and the base are generally used in an approximately stoichiometric ratio, or an excess or deficit of one or the other component is used, up to about 10 mol%.

Catalysts are preferably to be understood as meaning conventional phase transfer catalysts, in particular tetrabutylammonium hydrogen sulfate and crown ethers such as [18] crown-6. The amount of catalyst is not critical; usually an amount of 5 to 100 mol%, based on the amount of the alkylating agent, is sufficient.

Usually you work at atmospheric pressure. Higher or lower pressure is possible, but generally has no advantages.

The 3-phenylurazil derivatives I and I 'can be obtained in the preparation as isomer mixtures, both E- / Z-isomer mixtures and enantiomer or diastereomer mixtures being possible. If desired, the isomer mixtures can be separated by the customary methods, for example by chromatography or by crystallization. Compounds of the formula I 'can also be prepared by methods known per se by derivatizing the substituents R ² ', for example by esterification, ether cleavage or transesterification. The 3-phenylurazil derivatives I and I 'are suitable as

Desiccants, especially for defoliation of cotton, and as defoliants to dry out the above-ground parts of plants in crop plants, for example potatoes, sunflowers, soybeans and rapeseed. This enables fully mechanized harvesting of these important crops. Also of economic interest is the ease of harvesting, which is made possible by the temporally concentrated dropping of the fruit or a reduction in the adherence to the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. They also lead to a uniform ripening of the crop.

The same mechanism, i.e. the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the

Plant is also essential for a well controlled defoliation of crops such as cotton in particular. In addition, the shortening of the time interval in which the individual cotton plants ripen leads to increased fiber quality after the harvest.

Compared to known defoliants, the compounds I and I 'act - at a comparable rate of application, much more strongly and - their action is much safer even at low temperatures.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.

The formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents. The following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, solvents such as aromatics (e.g. toluene, xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. Petroleum fractions), alcohols (e.g. methanol, ethanol, butanol, cyclohexanol), ketones (e.g. cyclohexanone, isophorone), amines (e.g. ethanolamine, N, N-dimethylformamide, N-methylpyrrolidone) and water; Carriers such as natural stone powder (e.g. kaolins,

Clays, talc, chalk) and synthetic rock flours (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose. Aqueous use forms can be prepared from emulsion concentrates, dispersions, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.

The alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin-,

Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta and octadecanols, as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, formaldehyde Naphthalene or the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensate oil, polyalkylene ether polyethylenethoxylated ethoxylated ethoxylated urethane, ethylenedoxyl ether, ethoxylated sulfonyl ether, ethoxylated sulfonyl ether, ethoxylated sulfonyl ether, ethoxylated sulfonyl ether, ethoxylated sulfonyl ether, ethoxylated sulfonyl ether in

Consideration.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, dung agents such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

The concentrations of the active ingredients I and I 'in the ready-to-use preparations are generally between about 0.01 and 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Examples of such preparations are:

I. a solution of 90 parts by weight of compound no. 1 and

10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for use in the form of tiny drops;

II. A mixture of 20 parts by weight of compound no. 2,

80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the adduct and 40 Moles of ethylene oxide to 1 mole of castor oil. By finely distributing the mixture in 100,000 parts by weight of water, a dispersion is obtained which contains 0.02% by weight of the active ingredient.

III. an aqueous dispersion of 20 parts by weight of the compound

No. 3, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. The mixture of this dispersion with 100,000 parts by weight of water contains 0.02% by weight of the active ingredient. IV. An aqueous dispersion of 20 parts by weight of the compound

No. 4, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. The mixture of this dispersion with 100,000 parts by weight of water contains 0.02% of the active ingredient;

V. a mixture of 80 ground in a hammer mill

Parts by weight of compound no. 2, 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid,

10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight in powder form Silica gel. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient; VI. an intimate mixture of 3 parts by weight of the compound

No. 1 and 97 parts by weight of finely divided kaolin. This dust contains 3% by weight of active ingredient;

VII. An intimate mixture of 30 parts by weight of the compound

No. 4, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which was sprayed onto the surface of this silica gel. This preparation gives the active ingredient good adhesion; VIII. A stable aqueous dispersion of 40 parts by weight of

Compound No. 1, 10 parts by weight of the sodium salt of a phenosulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;

IX. a stable oily dispersion of 20 parts by weight of compound no. 2, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 Parts by weight of a paraffinic mineral oil;

X. a mixture of 10 ground in a hammer mill

Parts by weight of compound no. 3, 4 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid,

20 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor, 38 parts by weight of silica gel and 38 parts by weight of kaolin. By finely distributing the mixture in 10,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.

The plants are usually sprayed or dusted with the active ingredients. The application rates of active ingredient are 0.001 to 5.0, preferably 0.01 to 2 kg / ha of active substance (a.S.) depending on the control target, season, target plants and growth stage.

In order to broaden the spectrum of activity and to achieve synergistic effects, the 3-phenylurazil derivatives I and I 'can be used with numerous representatives of other crop protection agents such as

Herbicides, growth regulators, pesticides, Fungicides and bactericides are mixed and applied together. For example, diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl carbamates, thiol carbamates, haloearbonic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1 come as mixing partners. 3-dione derivatives which carry a carboxy or carbimino group in the 2-position, quinolinecarboxylic acid derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy-, heteroaryloxyphenoxypropionic acids and their salts, esters and amides and others.

These agents can be mixed into the preparations of the 3-phenyluracil derivatives I in a weight ratio of 1: 100 to 100: 1, if desired only immediately before use (tank mix). Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added. Examples of use

6,7-Dihydrodipyridol (1,2-a: 2 ', 1'-c) pyridilium served as the comparative agent as the dibromide monohydrate salt (Diquat®) (comparative agent A)

and N-phenyl-N '- (1,2,3-thiadiazol-5-yl) urea (Dropp WP 50®) (comparative agent B)

All tested 3-phenylurazil derivatives I and the comparison substances A and B (in the form of their fully formulated commercial products) were suspended in water before their application, the amount of water in the formulations being the equivalent of 1000 l / ha in each case. Young, 4-leafed (without cotyledons) cotton plants of the Stoneville 825 variety served as test plants and were grown under greenhouse conditions (relative humidity 50 to 70%, day / night temperature 27/20 ° C).

Application example 1

The cotton plants were dripped wet with aqueous preparations (with the addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac® LF 700, based on the spray liquor) of the active compounds indicated. 13 days after drug application, the number of leaves dropped and the degree of defoliation in% were determined. No leaf fall occurred in the untreated control plants,

The results of Application Example 1 show that the

3-phenylurazil derivatives I or I 'lead to defoliation of the plants even at a low application rate. They are clearly superior to comparison means A and B. Example of use 2

The test was carried out as described above, but with evaluation 14 days after drug application. The comparative agent C

the 3-phenylurazil derivatives I listed below. The test results are summarized in the table and show that C compared to the comparative agent seeing advantageous results in the defoliation of cotton can be achieved.

Claims

1. Use of 3-phenylurazil derivatives of the general

Formula I.

where the substituents have the following meaning:

R ^{1 is} hydrogen, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, the formyl group, a C ₂ -C ₆ alkanoyl group, a C ₃ -C ₄ alkenyl group or a C ₃ -C ₄ alkynyl group;

R ^{2 is} a via -O-, -O-CO-, -O-CS- or -O-SO ₂ - bound

Group, a group -CO-NR ⁷ R ⁸ or -CO-R ⁹ ; R ³ halogen or cyano;

R ^{4 is} hydrogen or halogen;

R ^{5 is} hydrogen, halogen or a C ₁ -C ₄ alkyl group;

R ^{6 is} a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group; or R ⁵ and R ⁶ together form a tri- or tetramethylene chain,

R ⁷ , R ⁸

Hydrogen, a C ₁ -C ₈ -alkyl radical which can also carry one of the following substituents: cyano,

Nitro, hydroxyl, hydroxycarbonyl, C ₁ -C ₄ alkoxy,

C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkoxycarbonyl, C ₁ -C ₄ alkylsulfonyl or

Di (C ₁ -C ₄ alkyl) phosphono; - a C ₂ -C ₈ -AlkenyIrest, a C ₃ -C ₈ -AlkinyIrest, a C ₁ -C ₈ haloalkyl group, a C ₃ -C ₈ cycloalkyl, C ₁ -C ₈ alkoxy; - The phenyl radical or a phenyl-C ₁ -C ₄ -alkyl radical, * where a saturated five- to seven-membered ring with optionally 1 or 2 oxygen atoms as ring members can optionally be fused to the phenyl ring, and the phenyl rings in turn also have one to three Can carry substituents selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy, hydroxyl, hydroxycarbonyl and C ₂ -C ₅ alkoxycarbonyl; with the proviso that R ⁷ and R ⁸ do not both simultaneously represent a C ₁ -C ₈ alkoxy radical, or

R ⁷ and R ⁸ together with the common nitrogen atom form a four- to seven-membered heterocyclic ring which can also carry one to three C ₁ -C ₆ -alkyl groups, one of the ring members being -O-, -S-, -N =, -NH- or -N (C ₁ -C ₄ alkyl) - may be substituted;

R ⁹

a radical -OC (R ¹⁰ , R ¹¹ ) -CH ₂ -ON = C (R ¹² , R ¹³ ),

-O-CH ₂ -ON = C (R ¹² , R ¹³ ), -ON = C (R ¹⁴ , R ¹⁵ ), -OR ¹⁶ or -SR ¹⁷ where R ^{9 is} not -OC (R ¹⁰ , R ¹¹ ) - CH ₂ -ON = C (R ¹² , R ¹³ ),

-O-CH ₂ -ON = C (R ¹² , R ¹³ ) or -ON = C (R ¹⁴ , R ¹⁵ ) may mean if R ^{1 is} hydrogen; R ^{10 represents} hydrogen or C ₁ -C ₄ alkyl,

R ¹¹ denotes hydrogen, C ₁ -C ₄ alkyl, phenyl or benzyl,

R ^{12 represents} hydrogen or C ₁ -C ₆ alkyl,

R ^{13 represents} C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl or phenyl, or R ¹² and R ¹³ together represent a three- to six-membered alkylene chain, R ^{14 represents} C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylthio, C ₂ -C ₇ alkoxycarbonyl or C ₂ -C ₇ alkoxycarbonyl-C ₁ -C ₄ alkyl;

R ¹⁵ denotes C ₁ -C ₆ alkyl, trifluoromethyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxy-C ₁ -C ₄ -alkyl,

R ¹⁶ denotes C ₁ -C ₈ haloalkyl, C ₃ -C ₅ haloalkenyl or C ₃ -C ₅ haloalkynyl or - [C (R ¹⁸ , R ¹⁹ )] _m -Q, where the substituents R ¹⁸ and R ¹⁹ independently represent hydrogen or C ₁ -C ₃ alkyl, m represents 0.1 or 2 and

Q for

C ₃ -C ₇ cycloalkyl or a saturated three- to seven-membered heterocycle with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms and, if desired, a carbonyl group as a ring member, the cycles on each substitutable C atom being a C ₁ -C ₄ alkyl group can carry

or

Phenyl, which if desired can carry one to three radicals, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl,

C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio, and wherein the phenyl ring is also a fused-on five- to seven-membered carbocyclic ring or a fused-on heterocyclic ring with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as Can carry heteroatoms; R ¹⁷ denotes hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ alkenyl,

C ₃ -C ₈ alkynyl, C ₂ -C ₆ alkoxyalkyl, C ₃ -C ₈ cycloalkyl, which, if desired, can also carry one to 3 C ₁ -C ₄ alkyl groups, phenyl or benzyl; as well as the enol ethers of those compounds I in which R ¹ denotes a C ₁ -C ₄ alkyl, C ₂ -C ₅ alkenyl or C ₃ -C ₅ alkynyl group, unless R ₂ denotes a group above -O -SO ₂ - bound group or a group -CO-O-CH ₂ -CH ₂ -ON = C (R ¹² , R ¹³ ) with R ¹² and R ¹³ C ₁ -C ₄ alkyl, and the agriculturally useful salts and Enol ethers of those compounds of the formula I in which R ^{1 is} hydrogen. for desiccation and abscission of plant organs.

Use of 3-phenylurazil derivatives of the formula I according to claim 1, where R ^{2 has} one of the following meanings:

C ₁ -C ₈ alkoxy, C ₃ -C ₇ cycloalkoxy, C ₃ -C ₈ alkenoxy,

C ₃ -C ₆ alkynoxy,

C ₁ -C ₈ haloalkoxy, C ₃ -C ₉ haloalkenyloxy,

C ₃ -C ₈ haloalkynyloxy,

- Cyano-C ₁ -C ₈ alkoxy, nitro -C ₁ -C ₈ alkoxy, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₁ - C ₄ -alkoxy, C ₅ -C ₇ -cycloalkoxy-C ₁ -C ₄ -alkoxy, C ₃ -C ₈ -alkenyloxy-C ₁ -C ₄ -alkoxy, C ₃ -C ₈ -alkynyloxy-C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkoxy- C ₁ -C ₄ -alkoxy, di- (C ₁ -C ₄ -alkoxy) -C ₁ -C ₄ -alkoxy, C ₁ - C ₄ - haloalkoxy-C ₁ -C ₄ -alkoxy, C ₃ -C ₄ -haloalkenyloxy-C ₁ -C ₄ -alkoxy, - C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkoxy, C ₅ -C ₇ cycloalkylthio C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenylthio C ₁ -C ₄ alkoxy,

C ₃ -C ₆ alkynylthio-C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₃ -C ₆ alkenyloxy, C ₁ -C ₄ alkylthio-C ₃ -C ₆ alkenyloxy, C ₁ -C ₄ alkoxy-C ₃ -C ₆ alkynyloxy, C ₁ -C ₄ alkylthio-C ₃ -C ₆ -alkynyloxy,

- C ₁ -C ₄ alkylsulfinyl-C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylsulfonyl- C ₁ -C ₄ alkoxy, formyl-C ₁ -C ₄ alkoxy, alkylcarbonyl-C ₁ -C ₄ alkoxy, C ₂ -C ₅ alkoxycarbonyl-C ₁ -C ₄ alkoxy, - Tri- (C ₁ -C ₄ alkyl) silyl-C ₁ -C ₄ alkoxy, C ₂ -C ₈ alkylidene aminooxy-C ₁ -C ₄ alkoxy, - C ₁ -C ₄ alkoxy, which is substituted by hydroxyl , Formyl, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ haloalkylcarbonyl, or C ₂ -C ₅ alkoxycarbonyl, - Carbamoyl-C ₁ -C ₄ alkoxy, the nitrogen atom of which

if desired carry one or two C ₁ -C ₄ alkyl radicals or part of a 3- to 7-membered azaheterocyclic

Ring can be

- ß-Aminoethoxy, the nitrogen atom being unsubstituted or carrying a C ₁ -C ₄ alkyl radical and, if desired, a further C ₁ -C ₄ alkyl, formyl, C ₂ -C ₅ alkylcarbonyl or C ₂ -C ₅ alkoxycarbonyl radical or can be part of a 3- to 7-membered azaheterocyclic ring, - phenyl-C ₁ -C ₄ -alkoxy, phenoxy-C ₁ -C ₄ -alkoxy, phenoxy-

C ₃ -C ₄ -alkynyloxy, benzyloxy-C ₁ -C ₄ -alkoxy, phenylthio- C ₁ -C ₄ -alkoxy, phenylsulfinyl-C ₁ -C ₄ -alkoxy, phenylsulfonyl-C ₁ -C ₄ -alkoxy or benzoyl- C ₁ -C ₄ alkoxy, where each of these phenyl rings can, if desired, carry one to three substituents selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - haloalkoxy, hydroxyl, hydroxycarbonyl and C ₂ -C ₅ alkoxycarbonyl, - a saturated or partially or completely unsaturated 3- to 7-membered heterocyclyloxy -, Heterocyclyl-C ₁ -C ₄ alkoxy or heterocyclyloxy-C ₁ -C ₄ alkoxy group, where the heterocycles can carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and a sulfur atom, and wherein the heterocycles can carry one of the following radicals on each substitutable carbon atom: cyano, nitro, halogen, C ₁ -C ₄ -alky l, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy, formyloxy, C ₂ -C ₈ alkylcarbonyloxy, C ₄ -C ₈ -Cycloalkylcarbonyloxy, C ₃ -C ₈ -alkenylcarbonyloxy, C ₃ -C ₈ -alkynylcarbonyloxy, cyano-C ₃ -C ₆ -alkylcarbonyloxy, C ₂ -C ₈ -haloalkylcarbonyloxy, C ₃ -C ₆ -cycloalkyl-C ₂ -C ₅ -alkylcarbonyloxy, C ₁ -C ₄ alkoxy-C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ alkylcarbonyl-C ₂ -C ₅ alkylcarbonyloxy,

C ₂ -C ₈ alkoxycarbonyloxy, C ₆ -C ₈ cycloalkoxycarbonyloxy, C ₃ -C ₈ alkenylcarbonyloxy, C ₄ -C ₈ alkynyloxycarbonyloxy,

C ₂ -C ₈ haloalkoxycarbonyloxy, C ₃ -C ₆ cycloalkyl-C ₂ -C ₅ alkoxycarbonyloxy, C ₁ -C ₄ alkoxy-C ₂ -C ₅ alkoxycarbonyloxy, - C ₁ -C ₄ alkyl - (thiocarbonyl) oxy, C ₁ -C ₄ alkylthiocarbonyloxy, C ₁ -C ₆ alkoxy- (thiocarbonyl) oxy, C ₁ -C ₆ alkylthio- (thiocarbonyl) oxy,

Carbamoyloxy, which can carry one of the following:

C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, phenyl or Phenyl-C ₁ -C ₄ -alkyl, the phenyl rings in turn being able to carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy,

- N, N-di- (C ₁ -C ₄ alkyl) carbamoyloxy, N, N-di- (C ₃ -C ₄ alkenyl) carbamoyloxy, N- (C ₁ -C ₄ alkyl) -N - (C ₃ -C ₄ alkenyl) carbamoyl oxy,

Aziridinyl-carbonyloxy, azetanyl-carbonyloxy, pyrrolidinylcarbonyloxy, piperidinyl-carbonyloxy, azepanyl-carbonyloxy,

- N- (C ₁ -C ₄ alkyl) thiocarbamoyloxy, N, N- di- (C ₁ -C ₄ alkyl) thiocarbamoyloxy,

- Benzoyloxy, phenoxycarbonyloxy, phenyl (C ₁ -C ₄ alkyl) carbonyloxy, phenyl (C ₁ -C ₄ alkoxy) carbonyloxy, where the

If desired, phenyl rings can also carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl,

C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy,

a C ₂ -C ₅ -alkylcarbonyloxy group which is substituted by hydroxyl, formyloxy, alkylcarbonyloxy, alkoxycarbonyloxy, carbamoyloxy, N-alkylcarbamoyloxy, N, N-dialkyl-carbamoyloxy, aziridin-1-ylcarbonyloxy, azetan-1-yl-carbonyloxy, pyrrolidine 1-yl-carbonyloxy, piperidin-1-yl-carbonyloxy,

Azepan-1-yl-carbonyloxy, hydroxycarbonyl, alkoxycarbonyl, Haloalkoxycarbonyl, carbamoyl, N-alkylcarbamoyl, N, N-dialkylcarbamoyl, aziridin-1-yl-carbonyl, azetan-1-ylcarbonyl, pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl or azepan-1- yl-carbonyl, can be substituted, with the proviso that the sum of the carbon atoms is 2 to 10, - a saturated or partially or completely unsaturated 3- to 7-membered heterocyclylcarbonyloxy or heterocyclyl-C ₁ -C ₄ -alkylcarbonyloxy group, where the heterocycles can carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and the heterocycles can carry one of the following radicals on each substitutable carbon atom: cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy,

- C ₁ -C ₈ alkylsulfonyloxy, C ₁ -C ₅ alkoxysulfonyloxy, - the sulfamoyloxy group, the nitrogen atom of which two

carries the following radicals: hydrogen, C ₁ -C ₄ -alkyl and / or C ₃ -C ₆ -cycloalkyl, -aziridin-1-ylsulfonyloxy, azetan-1-ylsulfonyloxy, pyrrolidin-1-yl-sulfonyloxy, piperidin-1-yl -sulfonyloxy or azepan-1-yl-sulfonyloxy, - phenylsulfonyloxy or phenyl-C ₁ -C ₄ -alkylsulfonyloxy, where the phenyl rings of these groups can, if desired, also carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy,

C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy.

3. Use of 3-phenylurazil derivatives of the formula I according to claim 1 or 2 for defoliation of cotton.

4. A process for the desiccation and abscess of parts of plants, characterized in that a defoliantly effective amount of at least one 3-phenylurazil derivative of the formula I according to claim 1 or 2 is allowed to act on plants or their habitat.

5. The method according to claim 4, characterized in that 0.001 to 10 kg / ha of a 3-phenylurazil derivative I are allowed to act on plants or their habitat. 6. 3-phenylurazil derivatives of the general formula I '

where the substituents have the following meaning:

R ¹ '

a C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl group;

R ² '

C ₁ -C ₈ alkoxy, C ₃ -C ₇ cycloalkoxy, C ₃ -C ₈ alkenoxy,

C ₃ -C ₆ alkynoxy,

C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ haloalkenyloxy,

C ₃ -C ₈ haloalkynyloxy,

- Cyano-C ₁ -C ₈ alkoxy, nitro-C ₁ -C ₈ alkoxy, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₁ - C ₄ alkoxy,

C ₅ -C ₇ cycloalkoxy-C ₁ -C ₄ alkoxy, C ₃ -C ₈ alkenyloxy-C ₁ -C ₄ alkoxy, C ₃ -C ₈ alkynyloxy-C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxy, di- (C ₁ -C ₄ alkoxy) -C ₁ -C ₄ alkoxy, C ₁ -C ₄ - Haloalkoxy-C ₁ -C ₄ -alkoxy, C ₃ -C ₄ -halogenalkenyloxy-C ₁ -C ₄ -alkoxy,

- C ₁ -C ₄ alkylthio-C ₁ -C ₄ alkoxy, C ₅ -C ₇ cycloalkylthio- C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenylthio-C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkynylthio-C ₁ -C ₄ alkoxy

- C ₁ -C ₄ alkoxy-C ₃ -C ₆ -alkenyloxy, C ₁ -C ₄ -alkylthio- C ₃ -C ₆ -alkenyloxy, C ₁ -C ₄ -alkoxy-C ₃ -C ₆ -alkynyloxy,

C ₁ -C ₄ -alkylthio-C ₃ -C ₆ -alkynyloxy - C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylsulfonyl- C ₁ -C ₄ -alkoxy, formyl- C ₁ -C ₄ alkoxy, alkylcarbonylC ₁ -C ₄ alkoxy, C ₂ -C ₅ alkoxycarbonylC ₁ -C ₄ alkoxy, Tri- (C ₁ -C ₄ alkyl) silyl-C ₁ -C ₄ alkoxy, C ₂ -C ₈ alkylidene aminooxy-C ₁ -C ₄ alkoxy C ₁ -C ₄ alkoxy, which is substituted by hydroxyl, Formyl, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ haloalkylcarbonyl, or C ₂ -C ₅ alkoxycarbonyl,

Carbamoyl-C ₁ -C ₄ alkoxy, its nitrogen atom

if desired, carry one or two C ₁ -C ₄ alkyl radicals or can be part of a 3- to 7-membered azaheterocyclic ring, β-aminoethoxy, where the nitrogen atom is unsubstituted or a C ₁ -C ₄ alkyl radical and, if desired, a further C ₁ -C ₄ alkyl, formyl, C ₂ -C ₅ alkylcarbonyl or C ₂ -C ₅ alkoxycarbonyl radical or may be part of a 3- to 7-membered azaheterocyclic ring; Phenyl-C ₁ -C ₄ -alkoxy, phenoxy-C ₁ -C ₄ -alkoxy, phenoxy-C ₃ -C ₄ -alkynyloxy, benzyloxy-C ₁ -C ₄ -alkoxy, phenylthio-C ₁ -C ₄ -alkoxy, Phenylsulfinyl-C ₁ -C ₄ -alkoxy, phenylsulfonyl-C ₁ -C ₄ -alkoxy or benzoyl-C ₁ -C ₄ -alkoxy, where each of these phenyl rings can optionally carry one to three substituents selected from a group consisting of cyano , Nitro, halogen, C ₁ -C ₄ alkyl,

C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio,

C ₁ -C ₄ haloalkoxy, hydroxyl, hydroxycarbonyl and

C ₂ -C ₅ alkoxycarbonyl; a saturated or partially or completely unsaturated 3 to 7-membered heterocyclyloxy, heterocyclyl-C ₁ -C ₄ -alkoxy or heterocyclyloxy-C ₁ -C ₄ -alkoxy group, where the heterocycles can carry one to four heteroatoms from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and where the heterocycles can carry one of the following radicals on each substitutable C atom: cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy;

Formyloxy, C ₂ -C ₈ alkylcarbonyloxy, C ₄ -C ₈ cycloalkylcarbonyloxy, C ₃ -C ₈ alkenylcarbonyloxy, C ₃ -C ₈ alkynylcarbonyloxy, cyano-C ₃ -C ₆ alkylcarbonyloxy, C ₂ -C ₈ - Haloalkylcarbonyloxy, C ₃ -C ₆ -cycloalkyl-C ₂ -C ₅ -alkylcarbonyloxy, C ₁ -C ₄ alkoxy-C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ alkylcarbonyl- C ₂ -C ₅ alkylcarbonyloxy,

C ₂ -C ₈ haloalkoxy-carbonyloxy, C ₃ -C ₆ cycloalkyl-C ₂ -C ₅ alkoxycarbonyloxy, C ₁ -C ₄ alkoxy-C ₂ -C ₅ alkoxycarbonyloxy,

- C ₁ -C ₄ -alkyl- (thiocarbonyl) oxy, C ₁ -C ₄ -alkylthio-carbonyl-oxy, C ₁ -C ₆ -alkoxy- (thiocarbonyl) oxy, C ₁ -C ₆ -alkylthio-

(thiocarbonyl) oxy,

Carbamoyloxy, which can carry one of the following:

C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, phenyl or Phenyl-C ₁ -C ₄ -alkyl, the phenyl rings in turn being able to carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy;

- N, N-di- (C ₁ -C ₄ alkyl) carbamoyloxy, N, N-di- (C ₃ -C ₄ alkenyl) carbamoyloxy, N- (C ₁ -C ₄ alkyl) -N - (C ₃ -C ₄ alkenyl) carbamoyloxy,

- Aziridinyl-carbonyloxy, Azetanyl-carbonyloxy, Pyrrolidinylcarbonyloxy, Piperidinyl-carbonyloxy, Azepanyl-carbonyloxy, - N- (C ₁ -C ₄ alkyl) thiocarbamoyloxy, N, N-Di- (C ₁ -C ₄ alkyl) - thiocarbamoyloxy,

- Benzoyloxy, phenoxycarbonyloxy, phenyl- (C ₁ -C ₄ -alkyl) -carbonyloxy, phenyl- (C ₁ -C ₄ -alkoxy) -carbonyloxy, where the phenyl rings can optionally carry one to three substituents selected from a group from cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ - haloalkoxy;

a C ₂ -C ₅ -alkylcarbonyloxy group which is substituted by hydroxyl, formyloxy, alkylcarbonyloxy, alkylcarbonyloxy, alkoxycarbonyloxy, carbamoyloxy, N-alkylcarbamoyloxy, N, N-dialkylcarbamoyloxy, aziridin-1-ylcarbonyloxy, azetan-1-yl-carbonyloxy, pyrrolidine 1-yl-carbonyloxy, piperidin-1-yl-carbonyloxy, azepan-1-yl-carbonyloxy, hydroxycarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, carbamoyl, N- Alkylcarbamoyl, N, N-dialkylcarbamoyl, aziridin-1-yl-carbonyl, azetan-1-ylcarbonyl, pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl or azepan-1-yl-carbonyl, can be substituted,

with the proviso that the sum of the carbon atoms is 2 to 10;

- A saturated or partially or completely unsaturated 3- to 7-membered heterocyclylcarbonyloxy or heterocyclyl-C ₁ -C ₄ -alkylcarbonyloxy group, the

Heterocycles can carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and the heterocycles can carry one of the following radicals on each substitutable C atom: cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy, - C ₁ -C ₈ alkylsulfonyloxy, C ₁ -C ₅ -alkoxysulfonyloxy, - the sulfamoyloxy group, the nitrogen atom of which two

carries the following radicals: hydrogen, C ₁ -C ₄ -alkyl and / or C ₃ -C ₆ -cycloalkyl; - Aziridin-1-ylsulfonyloxy, Azetan-1-ylsulfonyloxy, Pyrrolidin-1-yl-sulfonyloxy, Piperidin-1-yl-sulfonyloxy or Azepan-1-yl-sulfonyloxy;

Phenylsulfonyloxy or phenyl-C ₁ -C ₄ -alkylsulfonyloxy, where the phenyl rings of these groups can, if desired, also carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ alkoxy,

C ₁ -C ₄ alkylthio and C ₁ -C ₄ haloalkoxy;

R ³

Halogen or cyano;

R ⁴

Hydrogen or halogen;

R ⁵

Hydrogen, halogen or a C ₁ -C ₄ alkyl group; R ⁶

a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group; or

R ⁵ and R ⁶ together form a tri or tetramethylene chain.