DE19924805A1

DE19924805A1 - New benzyl, benzoyl or anilino-substituted triazinedionethiones, useful as pre- or post-emergence, total or selective herbicides

Info

Publication number: DE19924805A1
Application number: DE1999124805
Authority: DE
Inventors: Olaf Menke; Markus Menges; Gerhard Hamprecht; Michael Puhl; Robert Reinhard; Ingo Sagasser; Cyrill Zagar; Karl-Otto Westphalen; Martina Otten; Helmut Walter
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1999-05-29
Filing date: 1999-05-29
Publication date: 2000-11-30

Abstract

5-Benzyl-, 5-benzoyl- or 5-anilino-triazinedionethiones (I) are new. Triazinedionethiones of formula (I) and their salts and enol ethers are new. X = CH2, C(O) or NH; R1, R2 = Me or NH2; R3 = H, CN, SCN, halo, T', OT' or ST'; T' = 1-4C haloalkyl; R4 = as R4; T, alkenyloxy or alkynyloxy; alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkylaminocarbonyl, hydroxyalkylcarbonyl, NHSO2T or NH2 (all optionally substituted (os) by OT, COOT, NH2 or NHSO2T); T = 1-4C alkyl; one of R5, R6 = H, CN, NO2, halo or OT; the other R5, R6 = H, CN, NO2, halo or NH2; alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, alkenyloxy, 5-7C cycloalkenyloxy, alkenylthio, alkynylthio, alkylcarbonyloxy, alkylcarbonylthio, alkoxycarbonyloxy, alkenylcarbonyloxy, alkenylcarbonylthio, alkynylcarbonyloxy, alkynylcarbonylthio, alkylsulfonyl or alkylsulfonyloxy (all os by 1-4 R'6);-C(Y)-R14, -C(R14)(Z1R15)(Z2R16), C(R14)=C(R17)-CN, C(R14)=C(R17)-COR18, CHR14CHR17-COR18, C(R14)=C(R17)CH2COR18, C(R14)=C(R17)-C(R19)=C(R20)-COR18, C(R14)=C(R17)-CH2CHR21-COR18, COOR22, -CC-CONHOR9, -CC-CON(R22)OR9, -CC-CSNHOR9, -CC-CSN(R22)OR9, -CC-C(R10)=NOR9, -C(R14)=C(R17)-CONHOR9, C(R14)=C(R17)-CON(R22)OR9, C(R14)=C(R17)-CSNHOR9, C(R14)=C(R17)-CSN(R22)OR9, C(R14)=C(R17)-C(R10)=NOR9, NR24R25, -CC-Q or C(R14)=C(R17)-Q; or (iv) CON(R22)OR9, -C(R10)=NOR9, -C(Z1R15)(Z2R16)OR23, -C(Z1R15)(Z2R16)SR23, -C(Z1R15)(Z2R16)NR24R25, Q, COOR23, COSR23, alkylthioalkylcarbonyl or alkyliminooxycarbonyl; R'6 = halo, NO2, CN, OH, cycloalkyl, alkoxy, cycloalkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, 1-6C alkylideneaminooxy, Ph', OPh', SO2Ph', Het, -O-Het, =O, COR7, COOR7, COSR7, CONR7R8, OCOCR7, OCOOR7, OCOSR7, OCOCNR7R8, NR7R8, =NOR9, -C(R10)=NOR9 or SiR11R12R13; Ph' = phenyl (os by 1-3 of halo, NO2, CN, alkyl, haloalkyl, alkoxy and alkoxycarbonyl); Het = 3-7 heterocyclyl (os by 1-3 of halo, NO2, CN, alkyl, haloalkyl, alkoxy and alkylcarbonyl); Z1, Z2 = O or S; Q = (a); Q1 = 1-3C alkylene (os by alkyl); Q2 = O or S; R7 = H, alkyl, cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, alkoxyalkyl, alkoxycarbonylalkyl, (3-6C) alkenyloxycarbonylalkyl, Ph' or Ph'-alkyl; R8 = H, OH, alkyl, cycloalkyl, alkoxy, alkoxycarbonylalkoxy, 3-6C alkenyl or 3-6C alkenyloxy; NR7R8 = Het; R9 = H, alkyl, haloalkyl, cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, alkylcarbonylakyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkylcarbonyloxyalkyl or Ph'-alkyl; R10 = H or halo; alkyl, haloalkyl, alkoxy, haloalkoxy, 3-6C alkenyloxy, alkylthio, haloalkylthio, alkylcarbonyloxy, haloalkylcarbonyloxy, alkylsulfonyloxy or haloalkylsulfonyloxy (all os by OH, CN, COOH, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, mono- or dialkylaminocarbonyl or alkylcarbonyloxy); 3-7 azaheterocycle, bonded at N via a carbonyl bridge; alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxycarbonyloxy, alkylcarbonylthio, haloalkylcarbonylthio, alkoxycarbonylthio, alkenyl, alkenylthio, 3-6C alkynyl, 3-6C alkynyloxy, 3-6C alkynylthio, alynylcarbonyloxy, 3-6C alkynylsulfonyloxy, cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylcarbonyloxy or cycloalkylsulfonyloxy; or Ph', Ph'O, Ph'S, Ph'COO, Ph'SO2O, Ph'-alkyl, Ph'-alkoxy, Ph'-alkylthio, or Ph'-alkylsulfonyloxy; R14 = H, CN, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl or alkoxycarbonyl; R15, R16 = alkyl, haloalkyl, 3-6C alkenyl, 3-6C alkynyl or alkoxyalkyl; R15 + R16 = 2-4 (un)saturated C, substituted by 1-3 of CN, NO2, halo, alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, 3-6C alkenyloxyalkyl, (3-6C) alkynyloxyalkyl, cycloalkyl, cycloalkoxy, COOH, alkoxycarbonyl, alkylcarbonyloxy or Ph' and/or having 1 or 2 members forming part of a 3-7 ring, and os by 1 or 2 of CN, alkyl, alkenyl, alkoxy, cyanoalkkyl, haloalkyl and alkoxycarbonyl; R17 = H, CN, halo, alkyl, haloalkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl; R18 = H, OR23 SR23, alkyl (os by 1 or 2 alkoxy), alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylthioalkyl, alkyliminooxy, NR24R25 or Ph'; Ph'' = phenyl (os by 1-3 of CN, NO2, halo, alkyl, 3-6C alkenyl, haloalkyl, alkoxy and alkoxycarbonyl); R19 = H, CN, halo, alkyl, 3-6C alkenyl, 3-6C alkynyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, NR24R25 or Ph''; R20 = H, CN, halo, alkyl, alkoxy, haloalkyl, alkylcarbonyl or alkoxycarbonyl; R21 = H, CN, alkyl or alkoxycarbonyl; R22, R23 = H; alkyl, haloalkyl, alkenyl or alkynyl (all os by 1 or 2 of CN, halo, OH, COOH, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, (3-6C) alkenyloxycarbonyl or 3-7 azaheterocycle (optionally containing O or S), bonded at N via a carbonyl bridge); or alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, mono- or dialkylaminoalkyl, alkoxyiminoalkyl, cycloalkyl, Ph' or Ph'-alkyl; R24, R25 = H, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl (os in the alkenyl part by 1-3 halo and CN), alkylsulfonyl, alkoxycarbonylalkylsulfonyl, Ph'', Ph''SO2, Ph''CH2 or Ph''CH2SO2; NR24R25 = (un)saturated 4-7 ring, optionally containing a further O, S, N, NH or N(alkyl); Y = O, S or N(R28); R28 = H, OH, alkyl, 3-6C alkenyl, 3-6C alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, cycloalkoxy, 5-7C cycloalkenyloxy, haloalkoxy, 3-6C haloalkenyloxy, hydroxyalkoxy, cyanoalkyl, cycloalkylalkoxy, alkoxyalkoxy, alkoxy-(3-6C) alkenyloxy, alkylcarbonyloxy, haloalkylcarbonyloxy, alkylcarbonylalkyl, alkylcarbonylalkoxy, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, alkylthioalkoxy, dialkylaminoalkoxy or Ph''; Ph''-alkoxy, Ph''-(3-6C) alkenyloxy or Ph''-(3-6C) alkynyloxy ( 1 or 2 CH2 in the C chains may be replaced by O, S or N(alkyl)); Het, Het-alkoxy, Het-(3-6C) alkenyloxy or Het-(3-6C) alkynyloxy (1 or 2 CH2 in the C chains may be replaced by O, S or N(alkyl)); or NR29R30; R29, R30 = H, alkyl, 3-6C alkenyl, 3-6C alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl (os in the alkenyl part by 1-3 of halo and CN) or Ph''; and NR29R30 = (un)saturated 4-7 ring, optionally containing a further O, S, N, NH or N(alkyl). An Independent claim is included for the preparation of (I).

Description

Die vorliegende Erfindung betrifft neue 5-(Benz(o)yl/An ilino)triazindionthione der Formel I
The present invention relates to new 5- (benz (o) yl / an ilino) triazinedione thiones of the formula I.

wobei die Variablen folgende Bedeutungen haben:
X -CH₂, -C(=O)-oder -NH-;
R¹,R² Methyl oder Amino;
R³ Wasserstoff, Cyano, Thiocyanato, Halogen, C₁-C₄-Haloge nalkyl, C₁-C₄-Halogenalkoxy oder C₁-C₄-Halogenalkylthio;
R⁴ Wasserstoff, Cyano, Halogen, Thiocyanato, C₁-C₄-Haloge nalkyl, C₁-C₄-Halogenalkoxy, C₁-C₄-Halogenalkylthio, C₁-C₄-Alkoxy, C₂-C₆-Alkenoxy, C₂-C₆-Alkinoxy, C₁-C₆-Alko xycarbonyl, C₂-C₆-Alkenoxycarbonyl, C₂-C₆-Alkinoxycarbo nyl, C₁-C₆-Alkylaminocarbonyl, C₁-C₆-Hydroxyalkylcarbonyl, C₁-C₄-Alkylsulfonylamino oder Amino, wobei die letzten 7 Reste einen der folgenden Substituenten tragen können: C₁-C₄-Alkoxy, C₁-C₄-Alkoxycarbonyl, Amino oder C₁-C₄-Al kylsulfonylamino
R⁵ an Position α oder β Wasserstoff, Cyano, Nitro, Halogen oder C₁-C₄-Alkoxy;
R⁶ an Position α, wobei R⁵ dann an Position β steht,
where the variables have the following meanings:
X -CH ₂ , -C (= O) -or -NH-;
R ¹ , R ^{2 are} methyl or amino;
R ^{3 is} hydrogen, cyano, thiocyanato, halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio;
R ^{4 is} hydrogen, cyano, halogen, thiocyanato, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkoxy, C ₂ -C ₆ alkenoxy , C ₂ -C ₆ alkynoxy, C ₁ -C ₆ alkoxycarbonyl, C ₂ -C ₆ alkenoxycarbonyl, C ₂ -C ₆ alkynoxycarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ hydroxyalkylcarbonyl , C ₁ -C ₄ alkylsulfonylamino or amino, where the last 7 radicals can carry one of the following substituents: C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, amino or C ₁ -C ₄ alkylsulfonylamino
R ⁵ at position α or β is hydrogen, cyano, nitro, halogen or C ₁ -C ₄ alkoxy;
R ⁶ at position α, where R ^{5 is} then at position β,

1. hydrogen, cyano, nitro, halogen, amino,
2. C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cyeloalkylthio, C 2 -C 6 alkenyloxy, C 5 -C 7 cyclo alkenyloxy , C 2 -C 6 alkenylthio, C 2 -C 6 alkynyloxy, C 2 -C 6 alkynylthio, (C 1 -C 6 alkyl) carbonyloxy, (C 1 -C 6 alkyl) carbonylthio, (C 1 -C 6 alkoxy) carboxyloxy, (C 2 -C 6 alkenyl) carbonyloxy, (C 2 -C 6 alkenyl) carbonyl thio, (C 2 -C 6 alkynyl) carbonyloxy, (C 2 -C 6 alkynyl carbonylthio, C 1 -C 6 alkylsulfonyl or C 1 -C 6 alkylsulfonyloxy, where each of the latter 18 radicals can optionally carry one to four substituents, each selected from the group consisting of

Halogen, nitro, cyano, hydroxy, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 alkenyl oxy, C 3 -C 6 alkynyloxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylidene aminoxy,

- The phenyl, phenoxy or phenylsulfonyl group, which may be unsubstituted or bear one to three sub-substituents, each selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl , C 1 -C 6 alkoxy and (C 1 -C 6 alkoxy) carbonyl,

- A 3- to 7-membered heterocyclyl or heterocyclyloxy group, which can carry one to three substituents, each selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy , C 1 -C 6 haloalkyl and (C 1 -C 6 alkyl) carbonyl,

- an oxygen atom bound via a double bond,

a group -CO-R 7 , -CO-OR 7 , -CO-SR 7 , -CO-N (R 7 ) R 8 , -OCO-R 7 , -OCO-OR 7 , -OCO-SR 7 , -OCO-N (R 7 ) R 8 or -N (R 7 ) R 8 ,

- A group = N-OR 9 , -C (R 10 ) = N-OR 9 or Si (R 11 , R 12 , R 13 ), where R 11 , R 12 and R 13 independently of one another for C 1 -C 6 Alkyl or C 2 -C 6 alkenyl;
3. -CY-R 14 , -C (R 14 ) (Z 1 R 15 ) (Z 2 R 16 ), where Z 1 and Z 2 each represent oxygen or sulfur, -C (R 14 ) = C (R 17 ) -CN, -C (R 14 ) = C (R 17 ) -CO-R 18 , -CH (R 14 ) -CH (R 17 ) -CO-R 18 , -C (R 14 ) = C ( R 17 ) -CH 2 -CO-R 18 , -C (R 14 ) = C (R 17 ) -C (R 19 ) = C (R 20 ) -CO-R 18 , -C (R 14 ) = C (R 17 ) -CH 2 -CH (R 21 ) -CO R 18 , -CO-OR 22 , -C ∼ C-CO-NH-OR 9 , -C ∼ C-CO-N (R 22 ) -OR 9 , -C = C-CS-NH-OR 9 , -C ∼ C-CS-N (R 22 ) -OR 9 , -C ∼ CC (R 10 ) = N-OR 9 , -C (R 14 ) = C (R 17 ) -CO-NH-OR 9 , -C (R 14 ) = C (R 17 ) -CO-N (R 22 ) -OR 9 , -C (R 14 ) = C (R 17 ) -CS-NH-OR 9 , -C (R 14 ) = C (R 17 ) -CS-N (R 22 ) -OR 9 , -C (R 14 ) = C (R 17 ) -C (R 10 ) = N-OR 9 , -N (R 24 ) R 25 ,
where Alk is C 1 -C 3 alkylene which can carry a C 1 -C 6 alkyl substituent;
4. -CO-N (R 22 ) -OR 9 , -C (R 10 ) = N-OR 9 , -C (Z 1 R 15 ) (Z 2 R 16 ) OR 23 , -C (Z 1 R 15 ) (Z 2 R 16 ) SR 23 , -C (Z 1 R 15 ) (Z 2 R 16 ) NR 24 R 25 ,
-COO-R 23 , -COS-R 23 , -CON (R 24 ) R 25 , C 1 -C 6 alkylthio- (C 1 -C 6 alkyl) carbonyl or (C 1 -C 6 alkyl) iminooxycarbonyl ,

R⁷ R ⁷

für Wasserstoff, C₁ for hydrogen, C ₁

-C₆ -C ₆

-Alkyl, C₃ -Alkyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₃ Cycloalkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₃ Alkenyl, C ₃

-C₆ -C ₆

-Alkinyl, C₁ -Alkynyl, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkyl, (C₃ -alkyl, (C ₃

-C₆ -C ₆

-Alkenyloxy) - carbonyl-C₁ -Alkenyloxy) - carbonyl-C ₁

-C₆ -C ₆

-alkyl, Phenyl oder Phenyl-C₁ -alkyl, phenyl or phenyl-C ₁

-C₆ -C ₆

-alkyl, wobei die Phenylgruppe und der Phenyl-Ring der Phenyl alkylgruppe unsubstituiert sein oder einen bis drei Reste tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, C₁ alkyl, where the phenyl group and the phenyl ring of the phenyl alkyl group may be unsubstituted or may carry one to three radicals, each selected from the group consisting of halogen, nitro, cyano, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₁ Haloalkyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkyl)carbonyl
und
R⁸ -Alkyl) carbonyl
and
R ⁸

für Wasserstoff, Hydroxy, C₁ for hydrogen, hydroxy, C ₁

-C₆ -C ₆

-Alkyl, C₃ -Alkyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₁ Cycloalkyl, C ₁

-C₆ -C ₆

-Alkoxy, (C₁ -Alkoxy, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkoxy, C₃ -alkoxy, C ₃

-C₆ -C ₆

-Alkenyl oder C₃ Alkenyl or C ₃

-C₆ -C ₆

-Alkenyloxy, stehen, oder R⁷ Alkenyloxy, or R ⁷

und R⁸ and R ⁸

bilden zusammen mit dem gemeinsamen Stickstoff eine 3- bis 7-gliedrige Heterocyclylgruppe, die ihrerseits ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, C₁ together with the common nitrogen form a 3- to 7-membered heterocyclyl group, which in turn can carry one to three substituents, each selected from the group consisting of halogen, nitro, cyano, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl C₁ Haloalkyl C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkyl)carbonyl;
R⁹ -Alkyl) carbonyl;
R ⁹

Wasserstoff, C₁ Hydrogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₃ Haloalkyl, C ₃

-C₆ -C ₆

-Cyclo alkyl, C₃ -Cyclo alkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₃ Alkenyl, C ₃

-C₆ -C ₆

-Alkinyl, Hydroxy-C₁ -Alkynyl, hydroxy-C ₁

-C₆ -C ₆

-alkyl, C₁ alkyl, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkyl, C₁ alkyl, C ₁

-C₆ -C ₆

-Alkylthio-C₁ -Alkylthio-C ₁

-C₆ -C ₆

-alkyl, Cyano-C₁ -alkyl, cyano-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl-C₁ -Alkyl) carbonyl-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkoxy) carbonyl-C₂ -Alkoxy) carbonyl-C ₂

-C₆ -C ₆

-alkenyl, (C₁ -alkenyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyloxy-C₁ -Alkyl) carbonyloxy-C ₁

-C₆ -C ₆

- alkyl oder Phenyl-C₁ - alkyl or phenyl-C ₁

-C₆ -C ₆

-alkyl, wobei der Phenylring gewünschtenfalls ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ -alkyl, where the phenyl ring can optionally carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₁ Haloalkyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R¹⁰
Alkoxy) carbonyl;
R ¹⁰

- hydrogen, halogen,
C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 alkenyloxy, C 1 -C 6 alkyl thio, C 1 -C 6 haloalkylthio, (C 1 -C 6 alkyl) carbonyl oxy, (C 1 -C 6 haloalkyl) carbonyloxy, C 1 -C 6 alkyl sulfonyloxy or C 1 -C 6 haloalkylsulfonyloxy, where the the latter 11 radicals can carry one of the following substituents: hydroxy, cyano, hydroxy carbonyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, (C 1 -C 6 alkyl) carbonyl, (C 1 -C 6 -Alkoxy) carbonyl, (C 1 -C 6 -alkylamino) carbonyl, di- (C 1 -C 6 -alkyl) amino carbonyl, (C 1 -C 6 -alkyl) carbonyloxy,
- one with the nitrogen atom via a carbonyl bridge bonded 3- to 7-membered azaheterocycle, the in addition to carbon ring members, an oxygen or can contain sulfur atom as a ring member,
- (C 1 -C 6 alkyl) carbonyl, (C 1 -C 6 haloalkyl) carbonyl, (C 1 -C 6 alkoxy) carbonyl, (C 1 -C 6 alkoxy) carbonyloxy, (C 1 -C 6- alkyl) carbonylthio, (C 1 -C 6 haloalkyl) carbonylthio, (C 1 -C 6 alkoxy) carbonylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkenylthio, C 3 -C 6 -Alkynyl, C 3 -C 6 -alkynyloxy, C 3 -C 6 -alkynylthio, (C 2 -C 6 -alkynyl) carbonyloxy, C 3 -C 6 -alkynylsulfonyloxy, C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio, (C 3 -C 6 -cycloalkyl) carbonyl oxy, CJ-C 6 -cycloalkylsulfonyloxy,
- Phenyl, phenoxy, phenylthio, benzoyloxy, phenyl sulfonyloxy, phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkoxy, phenyl-C 1 -C 6 -alkylthio, phenyl- (C 1 -C 6 -alkyl) carbonyloxy or phenyl- (C 1 -C 6 -alkyl) sulfonyloxy, where the phenyl rings of the latter 10 radicals may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and (C 1 -C 6 alkoxy) carbonyl;

R¹⁴ R ¹⁴

Wasserstoff, Cyano, C₁ Hydrogen, cyano, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₂ Haloalkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₂ Alkenyl, C ₂

-C₆ -C ₆

-Alkinyl, C₃ -Alkynyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₁ Cycloalkyl, C ₁

-C₆ -C ₆

-Alk oxy-C₁ -Alk oxy-C ₁

-C₆ -C ₆

-alkyl oder (C₁ -alkyl or (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R¹⁵ Alkoxy) carbonyl;
R ¹⁵

, R¹⁶ , R ¹⁶

unabhängig voneinander C₁ independently of one another C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogen alkyl, C₃ -Halogen alkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₃ Alkenyl, C ₃

-C₆ -C ₆

-Alkinyl, C₁ -Alkynyl, C ₁

-C₆ -C ₆

-Alkoxy- C₁ -Alkoxy- C ₁

-C₆ -C ₆

-alkyl oder
R¹⁵ -alkyl or
R ¹⁵

und R¹⁶ and R ¹⁶

zusammen eine gesättigte oder ungesättigte, zwei- bis viergliedrige Kohlenstoffkette, die einen Oxo substituenten tragen kann, wobei ein Glied dieser Kette durch ein den Variablen Z1 und Z2 nicht benachbartes Sau erstoff-, Schwefel- oder Stickstoffatom ersetzt sein kann, und wobei die Kohlenstoffkette noch ein bis drei Reste tragen kann, jeweils ausgewählt aus der Gruppe be stehend aus Cyano, Nitro, Amino, Halogen, C₁ together a saturated or unsaturated, two- to four-membered carbon chain which can carry an oxo substituent, wherein one link of this chain can be replaced by an oxygen, sulfur or nitrogen atom not adjacent to the variables Z1 and Z2, and the carbon chain still can carry one to three residues, each selected from the group consisting of cyano, nitro, amino, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₂ -Alkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy; C₂ -Alkoxy; C ₂

-C₆ -C ₆

-Alkenyloxy, C₂ Alkenyloxy, C ₂

-C₆ -C ₆

-Alkinyloxy, C₁ -Alkynyloxy, C ₁

-C₆ -C ₆

-Halogenalkyl, Cyano-C₁ Haloalkyl, cyano-C ₁

-C₆ -C ₆

-alkyl, Hydroxy-C₁ -alkyl, hydroxy-C ₁

-C₆ -C ₆

-alkyl, C₁ alkyl, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkyl, C₃ alkyl, C ₃

-C₆ -C ₆

-Alke nyloxy-C₁ Alkene nyloxy-C ₁

-C₆ -C ₆

-alkyl, C₃ alkyl, C ₃

-C₆ -C ₆

-Alkinyloxy-C₁ -Alkynyloxy-C ₁

-C₆ -C ₆

-alkyl, C₃ alkyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₃ Cycloalkyl, C ₃

-C₆ -C ₆

-Cycloalkoxy, Carboxy, (C₁ -Cycloalkoxy, carboxy, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, (C₁ -Alkoxy) carbonyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl oxy-C₁ -Alkyl) carbonyl oxy-C ₁

-C₆ -C ₆

-alkyl und Phenyl, das seinerseits unsubsti tuiert sein oder einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Halogen, C₁ alkyl and phenyl, which in turn can be unsubstituted or can carry one to three substituents, each selected from the group consisting of cyano, nitro, amino, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogen alkyl, C₁ -Halogen alkyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, und wobei ein oder zwei Glieder der Kohlenstoffkette auch Bestandteil eines drei- bis siebengliedrigen Ringes sein können, der ein oder zwei Heteroatome als Ringglieder enthalten kann, ausgewählt aus Sauerstoff, Schwefel, Stickstoff und durch C₁ Alkoxy) carbonyl, and wherein one or two links of the carbon chain can also be part of a three- to seven-membered ring, which can contain one or two heteroatoms as ring members, selected from oxygen, sulfur, nitrogen and by C ₁

-C₆ -C ₆

-Alkyl substituiertem Stick stoff, und der gewünschtenfalls seinerseits einen oder zwei der folgenden Substituenten tragen kann: Cyano, C₁ -Alkyl-substituted nitrogen and, if desired, can itself carry one or two of the following substituents: cyano, C ₁

-C₆ -C ₆

-Alkyl, C₂ -Alkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy, Cyano-C₁ -Alkoxy, cyano-C ₁

-C₆ -C ₆

-alkyl, C₁ alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl und (C₁ -Haloalkyl and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R¹⁷ Alkoxy) carbonyl;
R ¹⁷

Wasserstoff, Cyano, Halogen, C₁ Hydrogen, cyano, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogen alkyl, C₁ -Halogen alkyl, C ₁

-C₆ -C ₆

-Alkoxy, (C₁ -Alkoxy, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl oder (C₁ -Alkyl) carbonyl or (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R¹⁸ Alkoxy) carbonyl;
R ¹⁸

Wasserstoff, O-R²³ Hydrogen, OR ²³

, S-R²³ , SR ²³

, C₁ , C ₁

-C₆ -C ₆

-Alkyl, das noch einen oder zwei C₁ -Alkyl, the one or two C ₁

-C₆ -C ₆

-Alkoxysubstituenten tragen kann, C₂ Can carry alkoxy substituents, C ₂

-C₆ -C ₆

-Alkenyl, C₂ Alkenyl, C ₂

-C₆ -C ₆

-Alkinyl, C₁ -Alkynyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₃ Haloalkyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₁ Cycloalkyl, C ₁

-C₆ -C ₆

-Alkylthio-C₁ -Alkylthio-C ₁

-C₆ -C ₆

-alkyl, C₁ alkyl, C ₁

-C₆ -C ₆

-Alkyliminooxy, -N(R²⁴ -Alkyliminooxy, -N (R ²⁴

)R²⁵ ) R ²⁵

oder Phenyl, das unsubsti tuiert sein oder ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ or phenyl, which may be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₂ -Alkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Halogen alkyl, C₁ -Halogen alkyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, wobei R₂₃ -Alkoxy) carbonyl, where R ₂₃

für eine der Bedeutungen von R₂₂ for one of the meanings of R ₂₂

steht,
R¹⁹ stands,
R ¹⁹

Wasserstoff, Cyano, Halogen, C₁ Hydrogen, cyano, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₃ -Alkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₃ Alkenyl, C ₃

-C₆ -C ₆

-Alkinyl, C₁ -Alkynyl, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl, (C₁ -Alkyl) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, -N(R²⁶ -Alkoxy) carbonyl, -N (R ²⁶

)R²⁷ ) R ²⁷

, wobei R²⁶ , where R ²⁶

und R²⁷ and R ²⁷

für eine der Bedeutungen von R²⁴ for one of the meanings of R ²⁴

und R²⁵ and R ²⁵

stehen, oder Phenyl, das seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ stand, or phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogen alkyl, C₃ -Halogen alkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy) carbonyl;
R²⁰ Alkoxy) carbonyl;
R ²⁰

Wasserstoff, Cyano, Halogen, C₁ Hydrogen, cyano, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Alkoxy, C₁ Alkoxy, C ₁

-C₆ -C ₆

-Halogenalkyl, (C₁ -Haloalkyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl oder (C₁ -Alkyl) carbonyl or (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R²¹ Alkoxy) carbonyl;
R ²¹

Wasserstoff, Cyano, C₁ Hydrogen, cyano, C ₁

-C₆ -C ₆

-Alkyl oder (C₁ -Alkyl or (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R²² Alkoxy) carbonyl;
R ²²

Wasserstoff, C₁ Hydrogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₂ Haloalkyl, C ₂

-C₆ -C ₆

-Alkenyl oder C₂ Alkenyl or C ₂

-C₆ -C ₆

-Alkinyl, wobei die letztgenannten 4 Gruppen jeweils einen oder zwei der folgenden Reste tragen können: Cyano, Halogen, Hydroxy, Hydroxycarbonyl, C₁ Alkynyl, where the latter 4 groups can each carry one or two of the following radicals: cyano, halogen, hydroxy, hydroxycarbonyl, C ₁

-C₆ -C ₆

-Alkoxy, C₁ Alkoxy, C ₁

-C₆ -C ₆

-Alkylthio, (C₁ -Alkylthio, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl, (C₁ -Alkyl) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, (C₁ -Alkoxy) carbonyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyloxy, (C₃ -Alkyl) carbonyloxy, (C ₃

-C₆ -C ₆

-Alkenyloxy)carbonyl oder einen mit dem Stick stoffatom über eine Carbonylbrücke gebundenen 3- bis 7-gliedrigen Azaheterocyclus, der neben Kohlenstoff ringgliedern noch ein Sauerstoff- oder Schwefelatom als Ringglied enthalten kann;
oder (C₁ -Alkenyloxy) carbonyl or a 3- to 7-membered azaheterocycle bonded to the nitrogen atom via a carbonyl bridge, which in addition to carbon ring members can also contain an oxygen or sulfur atom as a ring member;
or (C ₁

-C₆ -C ₆

-Alkyl)carbonyl, (C₁ -Alkyl) carbonyl, (C ₁

-C₆ -C ₆

-Halogenalkyl)carbonyl, (C₁ -Haloalkyl) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, C₁ Alkoxy) carbonyl, C ₁

-C₆ -C ₆

-Alkylaminocarbonyl, Di-(C₁ -Alkylaminocarbonyl, di- (C ₁

-C₆ -C ₆

-alkyl)aminocarbonyl, C₁ -alkyl) aminocarbonyl, C ₁

-C₆ -C ₆

-Alkyloximino- C₁ -Alkyloximino- C ₁

-C₆ -C ₆

-alkyl, C₃ alkyl, C ₃

-C₆ -C ₆

-Cycloalkyl, oder (C₁ -Cycloalkyl, or (C ₁

-C₆ -C ₆

-Alkyl)carbonyl, (C₁ -Alkyl) carbonyl, (C ₁

-C₆ -C ₆

-Halogenalkyl)carbonyl, (C₁ -Haloalkyl) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, C₁ Alkoxy) carbonyl, C ₁

-C₆ -C ₆

-Alkylaminocarbonyl, Di-(C₁ -Alkylaminocarbonyl, di- (C ₁

-C₆ -C ₆

-alkyl)aminocarbonyl, C₁ -alkyl) aminocarbonyl, C ₁

-C₆ -C ₆

-Alkyloximino- C₁ -Alkyloximino- C ₁

-C₆ -C ₆

-alkyl, C₃ alkyl, C ₃

-C₆ -C ₆

-Cycloalkyl, Phenyl oder Phenyl-C₁ -Cycloalkyl, phenyl or phenyl-C ₁

-C₆ -C ₆

-alkyl, wobei die Phenylringe unsubstituiert sein oder ihrerseits ein bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ alkyl, where the phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₁ Haloalkyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl;
R²⁴ Alkoxy) carbonyl;
R ²⁴

, R²⁵ , R ²⁵

unabhängig voneinander für Wasserstoff, C₁ independently of one another for hydrogen, C ₁

-C₆ -C ₆

-Alkyl, C₂ -Alkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₂ Alkenyl, C ₂

-C₆ -C ₆

-Alkinyl, C₃ -Alkynyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₁ Cycloalkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₁ Haloalkyl, C ₁

-C₆ -C ₆

-Alko xy-C₁ -Alko xy-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl, (C₁ -Alkyl) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, (C₁ -Alkoxy) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl- C₁ -Alkoxy) carbonyl- C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl-C₂ -Alkoxy) carbonyl-C ₂

-C₆ -C ₆

-alkenyl, wobei die Alkenylkette zusätzlich ein bis drei Halogen- und/ oder Cyano-Reste tragen kann, oder für C₁ alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or for C ₁

-C₆ -C ₆

-Alkylsulfonyl, (C₁ Alkylsulfonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbo nyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkylsulfonyl, Phenyl, Phenylsulfonyl, Benzyl oder Benzylsulfonyl wobei die vier Phenylringe unsubsti tuiert sein oder ihrerseits einen bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe beste herid aus Cyano, Nitro. Halogen, C₁ -alkylsulfonyl, phenyl, phenylsulfonyl, benzyl or benzylsulfonyl where the four phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group best heride from cyano, nitro. Halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₃ Haloalkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl,
stehen oder wobei
R²⁴ Alkoxy) carbonyl,
stand or where
R ²⁴

und R²⁵ and R ²⁵

zusammen mit dem gemeinsamen Stickstoffatom einen gesättigten oder ungesättigten 4- bis 7-gliedrigen Azaheterocyclus bilden, der neben Kohlenstoffringgliedern gewünschtenfalls eines der folgenden Glieder enthalten kann: -O-, -S-, -N= , -NH- oder -N(C₁ together with the common nitrogen atom form a saturated or unsaturated 4- to 7-membered azaheterocycle which, if desired, can contain one of the following members in addition to carbon ring members: -O-, -S-, -N =, -NH- or -N (C ₁

-C₆ -C ₆

-Alkyl)-;
Y Sauerstoff, Schwefel oder -N(R²⁸ -Alkyl);
Y oxygen, sulfur or -N (R ²⁸

)-, wobei
R²⁸ )-, in which
R ²⁸

für Wasserstoff, Hydroxy, C₁ for hydrogen, hydroxy, C ₁

-C₆ -C ₆

-Alkyl, C₃ -Alkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₃ Alkenyl, C ₃

-C₆ -C ₆

-Alkinyl, C₃ -Alkynyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₁ Cycloalkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₁ Haloalkyl, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkyl, C₁ alkyl, C ₁

-C₆ -C ₆

-Alkoxy, C₃ Alkoxy, C ₃

-C₆ -C ₆

-Alkenyloxy, C₃ Alkenyloxy, C ₃

-C₆ -C ₆

-Alkinyloxy, C₃ -Alkynyloxy, C ₃

-C₆ -C ₆

-Cycloalkyloxy, C₅ Cycloalkyloxy, C ₅

-C₇ -C ₇

-Cycloalkenyl oxy, C₁ -Cycloalkenyl oxy, C ₁

-C₆ -C ₆

-Halogenalkoxy, C₃ -Haloalkoxy, C ₃

-C₆ -C ₆

-Halogenalkenyloxy, Hydroxy-C₁ -Halogenalkenyloxy, hydroxy-C ₁

-C₆ -C ₆

-alkoxy, Cyano-C₁ -alkoxy, cyano-C ₁

-C₆ -C ₆

-alkoxy, C₃ -alkoxy, C ₃

-C₆ -C ₆

-Cyclo alkyl-C₁ -Cyclo alkyl-C ₁

-C₆ -C ₆

-alkoxy, C₁ -alkoxy, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkoxy, C₁ -alkoxy, C ₁

-C₆ -C ₆

-Alkoxy-C₃ -Alkoxy-C ₃

-C₆ -C ₆

-alkenyloxy, (C₁ -alkenyloxy, (C ₁

-C₆ -C ₆

-Alkyl)carbonyloxy, (C₁ -Alkyl) carbonyloxy, (C ₁

-C₆ -C ₆

-Halogenalkyl)carbonyloxy, (C₁ -Haloalkyl) carbonyloxy, (C ₁

-C₆ -C ₆

-Alkyl)carbamoyl oxy, (C₁ -Alkyl) carbamoyl oxy, (C ₁

-C₆ -C ₆

-Halogenalkyl)carbamoyloxy, (C₁ -Halogenalkyl) carbamoyloxy, (C ₁

-C₆ -C ₆

-Alkyl) carbonyl-C₁ -Alkyl) carbonyl-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl-C₁ -Alkyl) carbonyl-C ₁

-C₆ -C ₆

-alkoxy, (C₁ -alkoxy, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkoxy) carbonyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkoxy, C₁ -alkoxy, C ₁

-C₆ -C ₆

-Alkylthio-C₁ -Alkylthio-C ₁

-C₆ -C ₆

-alkoxy, Di-(C₁ -alkoxy, di- (C ₁

-C₆ -C ₆

-alkyl)amino-C₁ -alkyl) amino-C ₁

-C₆ -C ₆

-alkoxy,
Phenyl, das seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ -alkoxy,
Phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogen alkyl, C₂ -Halogen alkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl,
Phenyl-C₁ Alkoxy) carbonyl,
Phenyl-C ₁

-C₆ -C ₆

-alkoxy, Phenyl-C₃ -alkoxy, phenyl-C ₃

-C₆ -C ₆

-alkenyloxy oder Phenyl- C₃ -alkenyloxy or phenyl- C ₃

-C₆ -C ₆

-alkinyloxy, wobei jeweils eine oder zwei Methylen gruppen der Kohlenstoffketten durch -O-, -S- oder -N(C₁ -alkynyloxy, where in each case one or two methylene groups of the carbon chains by -O-, -S- or -N (C ₁

-C₆ -C ₆

-Alkyl)- ersetzt sein können und wobei jeder Phenylring unsubstituiert oder seinerseits einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ -Alkyl) - can be replaced and each phenyl ring can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₂ Haloalkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl,
Heterocyclyl, Heterocyclyl-C₁ Alkoxy) carbonyl,
Heterocyclyl, heterocyclyl-C ₁

-C₆ -C ₆

-alkoxy, Heterocyclyl- C₃ -alkoxy, heterocyclyl- C ₃

-C₆ -C ₆

-alkenyloxy oder Heterocyclyl-C₃ -alkenyloxy or heterocyclyl-C ₃

-C₆ -C ₆

-alkinyloxy, wobei jeweils eine oder zwei Methylengruppen der Kohlenstoff ketten durch -O-, -S- oder -N(C₁ -alkynyloxy, where in each case one or two methylene groups of the carbon chains by -O-, -S- or -N (C ₁

-C₆ -C ₆

-Alkyl)- ersetzt sein können und wobei jeder Heterocyclus drei- bis 7-gliedrig ist und seinerseits einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ -Alkyl) - can be replaced and each heterocycle is three to seven-membered and in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₂ Haloalkyl, C ₂

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, oder -N (R²⁹ -Alkoxy) carbonyl, or -N (R ²⁹

) R³⁰ ) R ³⁰

,
wobei R²⁹ ,
where R ²⁹

und R³⁰ and R ³⁰

jeweils für Wasserstoff, C₁ each for hydrogen, C ₁

-C₆ -C ₆

-Alkyl, C₃ -Alkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₃ Alkenyl, C ₃

-C₆ -C ₆

-Alkinyl, C₃ -Alkynyl, C ₃

-C₆ -C ₆

-Cycloalkyl, C₁ Cycloalkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₁ Haloalkyl, C ₁

-C₆ -C ₆

-Alkoxy-C₁ -Alkoxy-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkyl)carbonyl, (C₁ -Alkyl) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)-carbonyl, (C₁ Alkoxy) carbonyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl-C₁ -Alkoxy) carbonyl-C ₁

-C₆ -C ₆

-alkyl, (C₁ -alkyl, (C ₁

-C₆ -C ₆

-Alkoxy)carbo nyl-C₂ -Alkoxy) carbonyl-C ₂

-C₆ -C ₆

-alkenyl, wobei die Alkenylkette zusätzlich ein bis drei Halogen- und/oder Cyano-Reste tragen kann, oder für Phenyl, das unsubstituiert sein oder seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, C₁ -alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or for phenyl, which can be unsubstituted or in turn can also carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen , C ₁

-C₆ -C ₆

-Alkyl, C₁ -Alkyl, C ₁

-C₆ -C ₆

-Halogenalkyl, C₃ Haloalkyl, C ₃

-C₆ -C ₆

-Alkenyl, C₁ Alkenyl, C ₁

-C₆ -C ₆

-Alkoxy und (C₁ -Alkoxy and (C ₁

-C₆ -C ₆

-Alkoxy)carbonyl, stehen,
oder R²⁹ -Alkoxy) carbonyl,
or R ²⁹

und R³⁰ and R ³⁰

bilden zusammen mit dem gemeinsamen Stickstoffatom einen gesättigten oder ungesättigten 4- bis 7-gliedrigen Heterocyclus, der neben Kohlenstoff ringgliedern gewünschtenfalls noch eines der folgenden Glieder enthalten kann: -O-, -S-, -N = , -NH- oder -N(C₁ together with the common nitrogen atom form a saturated or unsaturated 4- to 7-membered heterocycle which, in addition to carbon ring members, can optionally contain one of the following members: -O-, -S-, -N =, -NH- or -N ( C ₁

-C₆ -C ₆

-Alkyl)-;
sowie die landwirtschaftlich brauchbaren Salze und Enolether der Verbindungen I.-Alkyl);
and the agriculturally useful salts and enol ethers of the compounds I.

Außerdem betrifft die Erfindung
The invention also relates to

- The use of the compounds I as herbicides and / or for the desiccation and / or defoliation of plants,
- herbicidal agents and agents for desiccation and / or Defoliation of plants which the compounds I as contain effective substances,
- Process for the preparation of the compounds I and of herbicidal agents and agents for desiccation and / or Defoliation of plants using compounds I,
- methods of controlling undesirable plant growth and for the desiccation and / or defoliation of plants with the Compounds I, as well
- new intermediates of formulas III and IV.

Die bei der Definition von R¹, R³ bis R³⁰ und Alk genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenstoffketten, also alle Alkyl-, Halogenalkyl-, Hydroxy alkyl-, Cyanoalkyl-, Phenylalkyl-, Alkylen-, Alkoxy-, Halogen alkoxy-, Hydroxyalkoxy-, Cyanoalkoxy-, Alkylthio-, Halogenalkyl thio, Alkylsulfinyl-, Alkylsulfonyl-, Halogenalkylsulfonyl-, Alkylamino-, Dialkylamino-, Alkyloximino-, Alkyliminooxy-, Alkylidenaminoxy-, Alkenyl-, Alkenyloxy-, Halogenalkenyloxy-, Alkenylthio-, Alkinyl-, Alkinyloxy- und Alkinylthio-Teile können geradkettig oder verzweigt sein.The organic molecule parts mentioned in the definition of R ¹ , R ³ to R ³⁰ and Alk represent collective terms for individual lists of the individual group members. All carbon chains, that is to say all alkyl, haloalkyl, hydroxyalkyl, cyanoalkyl, phenylalkyl and alkylene -, alkoxy, haloalkoxy, hydroxyalkoxy, cyanoalkoxy, alkylthio, haloalkyl thio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkylideneamoxy, alkenyl, alkenyloxy , Haloalkenyloxy, alkenylthio, alkynyl, alkynyloxy and alkynylthio parts can be straight-chain or branched.

Halogenierte Substituenten tragen vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome.Halogenated substituents preferably carry one to five same or different halogen atoms.

Die Bedeutung Halogen steht jeweils für Fluor, Brom, Chlor oder Iod, insbesondere für Fluor oder Chlor.The meaning halogen stands for fluorine, bromine, chlorine or Iodine, especially for fluorine or chlorine.

Ferner stehen beispielsweise
Furthermore, for example

- C 1 -C 4 alkyl for: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethyl ethyl, in particular for methyl or ethyl;
- C 1 -C 4 haloalkyl for: a C 1 -C 4 alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 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, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2, 2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2 , 2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4th -Chlorbutyl, 4-bromobutyl or nonafluorobutyl, especially for chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
- C 1 -C 6 alkyl for: C 1 -C 4 alkyl as mentioned above, and z. B. n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2 -Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl , 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, especially for methyl, ethyl, n-propyl, 1-methylethyl , n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;
- C 1 -C 6 haloalkyl for: C 1 -C 6 alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. one of the radicals mentioned under C 1 -C 4 -haloalkyl or for 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5, 5,5-tri chloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6 Trichloro-1-hexyl or dodecafluorohexyl, especially for chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
- Hydroxy-C 1 -C 6 alkyl for: e.g. B. Hydroxymethyl, 2-Hydroxyeth-1-yl, 2-Hydroxy-prop-1-yl, 3-Hydroxy-prop-1-yl, 1-Hydroxy prop-2-yl, 2-Hydroxy-but-1-yl , 3-Hydroxy-but-1-yl, 4-Hydroxy-but-1-yl, 1-Hydroxy-but-2-yl, 1-Hydroxy-but-3-yl, 2-Hydroxy-but-3-yl , 1-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, especially for 2-hydroxyethyl;
- Cyano-C 1 -C 6 alkyl for: e.g. B. Cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyano prop-1-yl, 1-cyanoprop-2 -yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl , 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyano but-3-yl, 1-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop- 3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;
- Phenyl-C 1 -C 6 alkyl for: e.g. B. 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, 4-phenylbut-2-yl , 1- (phenylmethyl) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-1-yl or 1- (phenylmethyl) -prop-1-yl, especially for benzyl or 2- Phenyl ethyl;
- Phenyl- (C 1 -C 6 alkyl) carbonyloxy for: e.g. B. benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenyl prop-1-ylcarbonyloxy, 2-phenylprop-1-ylcarbonyloxy, 3-phenyl prop-1-ylcarbonyloxy, 1-phenylbut-1-ylcarbonyloxy, 2-phenyl but -1-ylcarbonyloxy, 3-phenylbut-1-ylcarbonyloxy, 4-phenylbut-1-ylcarbonyloxy, 1-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenyl but-2-ylcarbonyloxy, 1- (phenylmethyl) -eth-1-ylcarbonyloxy, 1- (phenylmethyl) -1- (methyl) -eth-1-ylcarbonyloxy or 1- (phenylmethyl) prop-1-ylcarbonyloxy, especially for Benzylcarbonyloxy or 2-phenylethylcarbonyloxy;
- Phenyl-C 1 -C 6 alkylsulfonyloxy for: e.g. B. Benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, 1-phenylprop-1-ylsulfonyloxy, 2-phenylprop-1-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-1-ylsulfonyloxy, 2-phenylbutyloxy -1-ylsulfonyloxy, 3-phenylbut-1-ylsulfonyloxy, 4-phenylbut-1-ylsulfonyloxy, 1-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloky, 3-phenylbut-2-ylsulfonyloxy, 4-phenyl but-2-ylsulfonyloxy, 1- (phenylmethyl) -eth-1-ylsulfonyloxy, 1- (phenylmethyl) -1- (methyl) -eth-1-ylsulfonyloxy or 1- (phenylmethyl) prop-1-ylsulfonyloxy, especially for Benzylsulfonyloxy or 2-phenylethylsulfonyloxy;
- (C 1 -C 6 alkyl) carbonyl for: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1- Methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl , 4-methylpentylcarbonyl, 1,1-dimethylbutyl carbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutyl carbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutyl carbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2- Ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, especially for methyl carbonyl, ethylcarbonyl or 1-methylethylcarbonyl;
- (C 1 -C 6 -alkyl) carbonyl-C 1 -C 6 alkyl for: by (C 1 -C 6 alkyl) - carbonyl as mentioned above substituted C 1 -C 6 alkyl, ie z. B. for methylcarbonylmethyl;
- (C 1 -C 4 alkyl) carboxyl for: methyl carboxyl, ethyl carboxyl, n-propyl carboxyl, 1-methylethyl carboxyl, n-butyl carboxyl, 1-methyl propyl carboxyl, 2-methyl propyl carboxyl or 1,1-dimethyl ethyl carboxyl, especially for methyl carboxyl;
- (C 1 -C 6 -Halogenalkyl) carbonyl for: a (C 1 -C 6 -alkyl) carbonyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichloro fluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethyl carbonyl, 2,2-difluoromethyl, 2,2-difyl Trifluoroethyl carbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropyl carbonyl, 3- Fluoropropylcarbonyl, 2,2-difluoropropylcarbonony1, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3, 3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropyl carbonyl, heptafluoropropylcarbonyl, 1- (fluoromethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2-bromethylcarbonyl , 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, (5-fluo r-1-pentyl) carbonyl, (5-chloro-1-pentyl) carbonyl, (5-bromo-1-pentyl) carbonyl, (5-iodo-1-pentyl) carbonyl, (5,5,5-trichloro- 1-pentyl) carbonyl, undecafluoropentylcarbonyl, (6-fluoro-1-hexyl) carbonyl, (6-chloro-1-hexyl) carbonyl, (6-bromo-1-hexyl) carbonyl, (6-iodo-1-hexyl) carbonyl, (6,6,6-trichloro-1-hexyl) carbonyl or dodecafluorohexyl carbonyl, especially for trifluoroacetyl;
- (C 1 -C 6 alkyl) carbonyloxy for: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butyl carbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropyl carbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentyl carbonyloxy, 2-methylpentylcarbonyl carbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutyl carbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutyl carbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutyl carbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutyl carbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy or 1-ethyl-2-methylpropylcarbonyloxy, especially for acetyloxy;
- (C 1 -C 6 -Halogenalkyl) carbonyloxy for: a (C 1 -C 6 -alkyl) carbonyloxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for . B. chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy, fluoroacetyloxy, difluoroacetyloxy, tri fluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethyl carbonyloxy, 2-bromoethylcarbonyloxyoxy, 2,2-chloro-2,2-carbonyloxy-2-oxy-2,2-oxy-2-oxy-2,2-oxy-2-oxy-2,2-oxy-2-oxy-2,2-oxy-2-oxy-2,2-yl-2,2-oxy-carbonyl-oxy-2-yl Trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2,2-difluoroethyl carbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-tri chloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy , 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3 , 3-trichloropropylcarbonyloxy, 2,2,3,3,3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1- (fluoromethyl) -2-fluoroethyl carbonyloxy, 1- (chloromethyl) -2-chloroethylcarbonyloxy, 1- (bromomethyl) -2-bromethylca rbonyloxy, 4-fluorobutylcarbonyl oxy, 4-chlorobutylcarbonyloxy, 4-bromobutyl or nonafluorobutyl, in particular for trifluoroacetoxy;
- (C 1 -C 6 alkyl) carbonyloxy C 1 -C 6 alkyl for: by (C 1 -C 6 alkyl) carbonyloxy as mentioned above substituted C 1 -C 6 alkyl, ie z. B. for methylcarbonyloxymethyl, ethylcarbonyloxy methyl, 1- (methylcarbonyloxy) ethyl, 2- (methylcarbonyloxy) ethyl, 2- (ethylcarbonyloxy) ethyl, 3- (methylcarbonyloxy) propyl, 4- (methoxycarbonyloxy) butyl, 5- (methoxycarbonyloxy) pentyl or 6- (methoxycarbonyloxy) hexyl;
- (C 1 -C 6 alkyl) carbonylthio for acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butyl carbonylthio, 1-methylpropylcarbonylthio, 2-methylpropyl carbonylthio, 1,1-dimethylethylcarbonylthio, n-pentyl carbonylthio -Methylbutylcarbonylthio, 2-methylbutyl carbonylthio, 3-methylbutylcarbonylthio, 1,1-dimethylpropyl carbonylthio, 1,2-dimethylpropylcarbonylthio, 2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexyl carbonylthio, 1-methylpentylcarbonylthio, 3-methylpentylcarbonylthio, 4-methylpentyl carbonylthio, 1,1-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio, 1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio, 1-ethylbutyl 2-ethylbutylcarbonylthio, 1,1,2-trimethylpropylcarbonylthio, 1,2,2-trimethylpropylcarbonylthio, 1-ethyl-1-methylpropyl carbonylthio or 1-ethyl-2-methylpropylcarbonylthio, especially for Ac etylthio;
- (C 1 -C 6 -Halogenalkyl) carbonylthio for: a (C 1 -C 6 -alkyl) carbonylthio radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for . B. chloroacetylthio, dichloroacetylthio, trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, tri fluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluorethylcarbonylthio, 2-chloroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-chloroethyl carbonylthio, -Tri fluoroethylcarbonylthio, 2-chloro-2-fluoroethylcarbonylthio, 2-chloro-2,2-difluoroethylcarbonylthio, 2,2-dichloro-2-fluoroethylcarbonylthio, 2,2,2-trichloroethylcarbonylthio, penta fluoroethylcarbonylthio, 2-fluoropropylcarbonylthio, 3- Fluoropropylcarbonylthio, 2,2-difluoropropylcarbonylthio, 2,3-di fluoropropylcarbonylthio, 2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio, 3,3,3-trifluoropropyl , 3,3-trichloropropylcarbonylthio, 2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropyl carbonylthio, 1- (fluoromethyl) -2-fluoroethylcarbonylthio, 1- (chloromethyl) -2-chloroethylcarbon ylthio, 1- (bromomethyl) - 2-bromethylcarbonylthio, 4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, especially for trifluoroacetylthio;
- C 1 -C 4 alkoxy for: OCH 3 , OC 2 H 5 , n-propoxy, OCH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, OCH 2 -CH (CH 3 ) 2 or OC (CH 3 ) 3 , especially for OCH 3 or OC 2 H 5 ;
- C 1 -C 6 alkoxy for: C 1 -C 4 alkoxy as mentioned above, and z. B. n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2 -Methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy , 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, especially for methoxy, ethoxy or 1-methylethoxy;
- C 1 -C 4 haloalkoxy for: a C 1 -C 4 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2 Trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-di chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2 , 2-difluoropropoxy, 2,3-di fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy , 2,2,3,3,3-pentafluoropropoxy, hepta fluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluoro butoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, especially for 2-chloroethoxy or 2,2,2-trifluoroethoxy;
- C 1 -C 6 haloalkoxy for: a C 1 -C 6 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. one of the radicals mentioned under C 1 -C 4 -haloalkoxy or for 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5th , 5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6 -Trichlor-1-hexoxy or dodecafluorohexoxy, especially for chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;
- Phenyl-C 1 -C 6 alkoxy for: e.g. B. benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 2-phenylbut-1- yl oxy, 3-phenylbut-1-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 or 1- (phenylmethyl) prop-1-yloxy , especially for benzyloxy or 2-phenylethoxy;
- Phenyl-C 1 -C 6 alkylthio for: e.g. B. benzylthio, 1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-1-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-1-ylthio, 1-phenylbut-1-ylthio, 2-phenylbut- 1-ylthio, 3-phenylbut-1-ylthio, 4-phenylbut-1-ylthio, 1-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 3-phenylbut-2 -ylthio, 4-phenylbut-2-ylthio, 1- (phenylmethyl) -eth-1-ylthio, 1- (phenylmethyl) -1- (methyl) - eth-1-ylthio or 1- (phenylmethyl) prop-1 -ylthio, especially for benzylthio or 2-phenylethylthio;
- (C 1 -C 4 alkoxy) carbonyl for: CO-OCH 3 , CO-OC 2 H 5 , n-propoxy carbonyl, CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, 1-methylpropoxy carbonyl, CO- OCH 2 -CH (CH 3 ) 2 or CO-OC (CH 3 ) 3 , especially for CO-OCH 3 , CO-OC 2 H 5 , CO-OCH (CH 3 ) 2 or CO-CH 2 -CH (CH 3 ) 2 ;
- (C 1 -C 6 alkoxy) carbonyl for: (C 1 -C 4 alkoxy) carbonyl as mentioned above, and z. B. n-pentoxycarbonyl, 1-methyl butoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxy carbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxy carbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl , 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3- Dimethyl butoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxy carbonyl, 1-ethyl-1-methyl-propoxycarbonyl or 1-ethyl-2-methyl-propoxycarbonyl, especially for Methoxycarbonyl, ethoxycarbonyl or 1-methylethoxycarbonyl;
- (C 1 -C 6 -alkoxy) carbonyloxy for: methoxycarbonyloxy, ethoxy carbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methyl propoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxy carbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxy carbonyloxy, 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxy carbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxy -Methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbonyloxy, 2,3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy, 2-ethoxy , 1,1,2-trimethylpropoxycarbonyloxy, 1,2,2-trimethylprop oxycarbonyloxy, 1-ethyl-1-methyl-propoxycarbonyloxy or 1-ethyl-2-methyl-propoxycarbonyloxy, especially f for methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxy carbonyloxy;
- (C 1 -C 6 alkoxy) carbonylthio for: methoxycarbonylthio, ethoxy carbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1,1-dimethylethoxycarbonylthio, n-pentoxycarbonate -Methylbutoxycarbonylthio, 2-methyl butoxycarbonylthio, 3-methylbutoxycarbonylthio, 2,2-dimethyl propoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxy carbonylthio, 1,1-dimethylpropoxycarbonylthio, 1,2-dimethyl propoxycarbonylthio, 1-methylpentoxycarbonylthiocarbonylthio, 2 3-methylpentoxycarbonylthio, 4-methyl pentoxycarbonylthio, 1,1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1,3-dimethylbutoxycarbonylthio, 2,2-dimethylbutoxycarbonylthio, 2,3-dimethylbutoxycarbonylthio, 3,3-dimethylbutoxycarbonylthio, 1-ethyl thio, 2-ethylbutoxycarbonylthio, 1,1,2-trimethylpropoxy carbonylthio, 1,2,2-trimethylpropoxycarbonylthio, 1-ethyl-1-methyl-propoxycarbonylthio or 1-ethyl-2-me thyl-propoxy carbonylthio, especially for methoxycarbonylthio, ethoxy carbonylthio or 1-methylethoxycarbonylthio;
- C 1 -C 6 alkylthio for: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2- Methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methyl pentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methyl pentylthio 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1, 2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, especially for methylthio or ethylthio;
C 1 -C 4 haloalkylthio for: C 1 -C 4 alkylthio partially or completely substituted by fluorine, chlorine and / or bromine, such as methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio, preferably methylthio or ethyl thio,
so z. B. difluoromethylthio, trifluoromethylthio, chloro-difluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-di fluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio , 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2- Bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3, 3-pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutyl , especially for trifluoromethylthio or difluoromethylthio;
- C 1 -C 6 -Halogenalkylthio for: C 1 -C 6 -alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for. B. one of the radicals mentioned under C 1 -C 4 -haloalkylthio or for 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodine pentylthio, undecafluoropentylthio, 6-fluorhexylthio or 6-chlorohexylthio, especially for chloromethylthio, fluoromethylthio , Difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio or 2,2,2-trifluoroethylthio;
- C 1 -C 6 alkylsulfinyl for: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2 -Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 3-methylpentylsulfinyl Methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1 , 1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, especially for methyl sulfinyl;
- C 1 -C 6 alkylsulfonyl for; Methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethyl ethylsulfonyl, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1 -Dimethyl propylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylsulfonyl , 2-dimethylbutylsulfonyl, 1,3-dimethylbutyl sulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutyl sulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2 , 2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, especially for methyl sulfonyl;
- C 1 -C 6 alkylsulfonyloxy for: methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, n-butylsulfonyloxy, 1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy, 1,1-dimethylethylsulfonyloxy, n-pentylsulfonyloxy, n- Methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, 1,1-dimethylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyloxy, 2,2-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy, n-hexylsulfonyloxy, 3 4-methylpentylsulfonyloxy, 1,1-dimethylbutyl sulfonyloxy, 1,2-dimethylbutylsulfonyloxy, 1,3-dimethylbutyl sulfonyloxy, 2,2-dimethylbutylsulfonyloxy, 2,3-dimethylbutyl sulfonyloxy, 3,3-dimethylbutylsulfonyloxy, 1-ethylbutyl sulfonyloxy Ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy, 1,2,2-trimethylpropylsulfonyloxy, 1-ethyl-1-methylpropylsulfonyloxy or 1-ethyl-2-methylpropylsulfonyloxy, especially for methylsulfonyloxy;
- C 1 -C 6 -Halogenalkylsulfonyloxy for: C 1 -C 6 -alkylsulfonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. ClCH 2 -SO 2 -O-, CH (Cl) 2 -SO 2 -O-, C (Cl) 3 -SO 2 -O-, FCH 2 -SO 2 -O-, CHF 2 -SO 2 - O-, CF 3 -SO 2 -O-, chlorofluoromethyl-SO 2 -O-, dichlorofluoromethyl-SO 2 -O-, chlorodifluoromethyl-SO 2 -O-, 1-fluoroethyl-SO 2 -O-, 2-fluoroethyl -SO 2 -O-, 2-chloroethyl-SO 2 -O-, 2-bromo ethyl-SO 2 -O-, 2-iodoethyl-SO 2 -O-, 2,2-difluoroethyl-SO 2 -O-, 2,2,2-trifluoroethyl-SO 2 -O-, 2-chloro-2-fluoroethyl-SO 2 -O-, 2-chloro-2,2-difluoroethyl-SO 2 -O-, 2,2-dichloro- 2-fluoroethyl- SO 2 -O-, 2,2,2-trichloroethyl-SO 2 -O-, C 2 F 5 -SO 2 -O-, 2-fluoropropyl-SO 2 -O-, 3-fluoropropyl- SO 2 -O-, 2,2-difluoropropyl-SO 2 -O-, 2,3-difluoropropyl-SO 2 -O-, 2-chloropropyl-SO 2 -O-, 3-chloropropyl-SO 2 -O- , 2,3-dichloropropyl-SO 2 -O-, 2-bromopropyl-SO 2 -O-, 3-bromopropyl-SO 2 -O-, 3,3,3-trifluoropropyl-SO 2 -O-, 3,3 , 3-Tri chloropropyl-SO 2 -O-, 2,2,3,3,3-pentafluoropropyl-SO 2 -O-, C 2 F 5 -CF 2 -SO 2 -O-, 1- (fluoromethyl) - 2-fluoroethyl-SO 2 -O-, 1- (chloromethyl) -2-chloroethyl-SO 2 -O-, 1- (bromomethyl) -2-bromoethyl-SO 2 -O-, 4-fluorobutyl- SO 2 -O-, 4-chlorobutyl-SO 2 -O-, 4-bromobutyl-SO 2 -O-, C 2 F 5 -CF 2 -CF 2 -SO 2 -O-, 5-fluoropentyl-SO 2 - O-, 5-chloropentyl-SO 2 -O-, 5-bromopentyl-SO 2 -O-, 5-iodopentyl-SO 2 -O-, 5,5,5-trichloropentyl-SO 2 -O-, C 2 F 5 -CF 2 -CF 2 -CF 2 -SO 2 -O-, 6-fluoro hexyl-SO 2 -O-, 6-chlorohexyl-SO 2 -O-, 6-bromohexyl-SO 2 -O-, 6- Iodine hexyl-SO 2 -O-, 6,6,6-trichlorohexyl-SO 2 -O- or dodecafluoro hexyl-SO 2 -O-, especially for CF 3 -SO 2 -O-;
- C 1 -C 4 alkylamino for: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino, in particular for methylamino or ethylamino;
- (C 1 -C 4 alkylamino) carbonyl for: CO-NH-CH 3 , CO-NH-C 2 H 5 , n-propylaminocarbonyl, CO-NH-CH (CH 3 ) 2 n-butylaminocarbonyl, 1-methylpropylaminocarbonyl , CO-NH-CH 2 -CH (CH 3 ) 2 or CO-NH-C (CH 3 ) 3 , in particular for CO-NH-CH 3 or CO-NH-C 2 H 5 ;
- (C 1 -C 6 alkylamino) carbonyl for: (C 1 -C 4 alkylamino) carbonyl as mentioned above and z. B. n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimylaminocarbonyl, 1-methylethylpylaminocarbonyl -Methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylamino carbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutyl aminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethyl butyl 1-ethylbutylaminocarbonyl, 2-ethylbutyl aminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylamino carbonyl or 1-ethyl-2-methylpropylaminocarbonyl, especially for CO-NH- CH 3 , CO-NH-C 2 H 5 or CO-NH-CH (CH 3 ) 2 ;
- Di- (C 1 -C 6 alkyl) aminocarbonyl for: e.g. B. N, N-dimethylamino carbonyl, N, N-diethylaminocarbonyl, N, N-dipropylamino carbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dibutyl aminocarbonyl, N, N-di- (1 -methylpropyl) aminocarbonyl, N, N-di- (2-methylpropyl) aminocarbonyl, N, N-di- (1,1-dimethyl ethyl) -aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl , N-methyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- (1,1-dimethylethyl) -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1- methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- (1,1-dimethylethyl) aminocarbonyl, N- (1-methylethyl) -N-propylaminocarbonyl, N-butyl-N- propyl aminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- (1,1-dimethylethyl) -N-propylaminocarbonyl, N-butyl-N- (1 -methylethyl) amino c arbonyl, N- (1-methylethyl) -N- (1-methylpropyl) aminocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1,1-dimethylethyl) -N- ( 1-methylethyl) aminocarbonyl, N-butyl-N- (1-methylpropyl) aminocarbonyl, N-butyl-N- (2-methylpropyl) amino carbonyl, N-butyl-N- (1,1-dimethylethyl) aminocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminocarbonyl, N- (1,1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or N- (1,1-dimethylethyl) -N- (2-methylpropyl ) aminocarbonyl, especially for N, N-dimethylaminocarbonyl or N, N-diethyl aminocarbonyl;
- (C 1 -C 6 alkyl) aminooxycarbonyl for: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methyl ethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methyl propyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1,1-dimethylethylimylyloxycarbonyl, n-propyliminooxycarbonyl -Methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1,1-dimethylpropyliminooxycarbonyl, 1,2-dimethylpropyliminooxycarbonyl, 2,2-dimethylpropyliminooxycarbonyl, 1-ethylpropyliminooxycarbonyl, n-hexyliminooxyylyloxy-methylyloxy-methylyl-1-methyloxy-methylyl-1-methyloxy-methyloxy-1-methyloxy-methyloxy-2-methyloxy-methyloxy-2-methyloxy-methyloxy-3-methyloxy-methyloxy-2-methyloxy-methyloxy-1-methyloxy-methyloxy-2-methyloxy-methyloxy-2-methyloxy-methyloxy-3-methyloxy-2-methyloxy-methyloxy-2-methyloxy-methyloxy-2-methyloxy-methyloxy-1-carbonyl carbonyl, 4-methylpentyliminooxycarbonyl, 1,1-dimethylbutyl iminooxycarbonyl, 1,2-dimethylbutyliminooxycarbonyl, 1,3-dimethylbutyliminooxycarbonyl, 2,2-dimethylbutyliminooxy carbonyl, 2,3-dimethylbutyliminooxycarbonyl, 3,3-dimethylbutyliminooxycarbonyl, 1-ethyloxybutyl 2-ethyl butyliminooxycarbonyl, 1,1,2-trimethylpropyliminooxycarbonyl, 1,2,2-trimethylpropyliminooxycarbonyl, 1-ethyl-1-methylpropyliminooxycarbonyl or 1-ethyl-2-methylpropyliminooxy carbonyl, especially for methyliminooxycarbonyl, ethyl iminooxycarbonyl or 1-methylethyliminooxycarbonyl;
C 1 -C 6 alkylidene aminoxy for: acetylidene aminoxy, 1-propylidene aminoxy, 2-propylidene aminoxy, 1-butylidene aminoxy, 2-butylidene aminoxy or 2-hexylidene aminoxy, in particular for acetylidene aminoxy or 2-propylidene aminoxy;
- C 1 -C 6 alkyliminooxy for: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methyl pentyliminooxy, 3-methylpentyliminooxy or 4-methylpentyl iminooxy, especially for methyliminooxy, ethyliminooxy or 1-methylethyliminooxy;
- C 1 -C 6 alkyloximino-C 1 -C 6 alkyl for: by C 1 -C 6 alkyloximino such as methoxyimino, ethoxyimino, 1-propoxyimino, 2-propoxy imino, 1-methylethoxyimino, n-butoxyimino, sec. -Butoxyimino, tert-butoxyimino, 1-methyl-1-propoxyimino, 2-methyl-1-prop oxyimino, 1-methyl-2-propoxyimino, 2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino, 3 -Pentoxyimino, 4-pentoxyimino, 1-methyl-1-butoxyimino, 2-methyl-1-butoxyimino, 3-methyl-1-butoxyimino, 1-methyl-2-butoxyimino, 2-methyl-2-butoxyimino, 3- Methyl-2-butoxyimino, 1-methyl-3-butoxyimino, 2-methyl-3-butoxyimino, 3-methyl-3-butoxyimino, 1,1-dimethyl-2-propoxyimino, 1,2-dimethyl-1-propoxyimino , 1,2-dimethyl-2-propoxyimino, 1-ethyl-1-propoxyimino, 1-ethyl-2-propoxyimino, n-hexoxyimino, 2-hexoxyimino, 3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino, 1-methyl -1-pent oxyimino, 2-methyl-1-pentoxyimino, 3-methyl-1-pentoxyimino, 4-methyl-1-pentoxyimino, 1-methyl-2-pentoxyimino, 2-methyl- 2-pentoxyimino, 3-methyl 2-pentoxyimino, 4-methyl-2-pento xy imino, 1-methyl-3-pentoxyimino, 2-methyl-3-pentoxyimino, 3-methyl-3-pentoxyimino, 4-methyl-3-pentoxyimino, 1-methyl-4-pentoxyimino, 2-methyl-4-pentoxyimino , 3-methyl-4-pentoxyimino, 4-methyl-4-pentoxyimino, 1, 1-dimethyl-2-butoxyimino, 1,1-dimethyl-3-butoxyimino, 1,2-dimethyl-1-butoxyimino, 1, 2-dimethyl-2-butoxyimino, 1,2-dimethyl-3-butoxyimino, 1,3-dimethyl-1-butoxyimino, 1,3-dimethyl-2-butoxyimino, 1,3-dimethyl-3-butoxyimino, 2, 2-dimethyl-3-butoxyimino, 2,3-dimethyl-1-butoxyimino, 2,3-dimethyl-2-butoxyimino, 2,3-dimethyl-3-butoxyimino, 3,3-dimethyl-1-butoxyimino, 3, 3-dimethyl-2-butoxyimino, 1-ethyl-1-butoxyimino, 1-ethyl-2-butoxyimino, 1-ethyl-3-butoxyxino, 2-ethyl-1-butoxyimino, 2-ethyl-2-butoxyimino, 2- Ethyl 3-butoxyimino, 1,1,2-trimethyl-2-propoxyimino, 1-ethyl-1-methyl-2-propoxyimino, 1-ethyl-2-methyl-1-propoxyimino and 1-ethyl-2-methyl -2- propoxyimino, substituted C 1 -C 6 alkyl, e.g. B. for methoxyiminomethyl;
- C 1 -C 6 alkoxy-C 1 -C 6 alkyl for: substituted by C 1 -C 6 alkoxy as mentioned above C 1 -C 6 alkyl, that is, for. B. for methoxymethyl, ethoxymethyl, n-propoxymethyl, (1-methyl ethoxy) methyl, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1,1-dimethylethoxy) methyl, 2- (methoxy ) ethyl, 2- (ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methyl propoxy) ethyl, 2- ( 2-methylpropoxy) ethyl, 2- (1,2-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-prop oxy) propyl, 2- (1-methylethoxy) propyl , 2- (n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy ) - propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methyl propoxy) propyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-butoxy ) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1,1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n -Propoxy) butyl, 3- (1-methylethoxy) butyl, 3- ( n-butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1,1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl , 4- (n-prop oxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- ( 1,1-dimethylethoxy) butyl, especially for methoxymethyl or 2-methoxyethyl;
- C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy for: substituted by C 1 -C 6 -alkoxy as mentioned above C 1 -C 6 -alkoxy, ie z. B. for methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, (1-methylethoxy) methoxy, n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1,1-dimethylethoxy) methoxy, 2- (methoxy ) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (1-methyl propoxy) ethoxy, 2- ( 2-methylpropoxy) ethoxy, 2- (1,1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (n-propoxy) propoxy, 2- (1-methylethoxy) propoxy, 2- (n-but oxy) propoxy, 2- (1-methylpropoxy) propoxy, 2- (2-methylprop oxy) propoxy, 2- (1,1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3- ( Ethoxy) propoxy, 3- (n-propoxy) propoxy, 3- (1-methylethoxy) propoxy, 3- (n-butoxy) propoxy, 3- (1-methyl propoxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- (1,1-dimethylethoxy) propoxy, 2- (methoxy) butoxy, 2- (ethoxy) butoxy, 2- (n-propoxy) butoxy, 2- (1-methylethoxy) butoxy, 2- (n-butoxy ) butoxy, 2- (1-methylpropoxy) butoxy, 2- (2-methylpropoxy) butoxy, 2- (1,1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy) butoxy, 3- (n - Propoxy) butoxy, 3- (1-methylethoxy) butoxy, 3- (n-butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- (1,1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (ethoxy) butoxy, 4- (n-propoxy) butoxy, 4- (1-methyl ethoxy) butoxy, 4- (n-butoxy) butoxy, 4- (1-methylpropoxy ) butoxy, 4- (2-methylpropoxy) butoxy, 4- (1,1-dimethylethoxy) butoxy, 5- (methoxy) pentoxy, 5- (ethoxy) pentoxy, 5- (n-propoxy) pentoxy, 5- (1st -Methylethoxy) pentoxy, 5- (n-butoxy) pentoxy, 5- (1-methylpropoxy) pentoxy, 5- (2-methylpropoxy) pentoxy, 5- (1,1-dimethylethoxy) pentoxy, 6- (methoxy) hexoxy, 6- (ethoxy) hexoxy, 6- (n-propoxy) hexoxy, 6- (1-methylethoxy) hexoxy, 6- (n-butoxy) hexoxy, 6- (1-methylpropoxy) hexoxy, 6- (2- Methylpropoxy) hexoxy or 6- (1,1-dimethylethoxy) hexoxy, especially for methoxy methoxy or ethoxymethoxy;
- (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 alkoxy of: by (C 1 -C 6 alkoxy) - carbonyl as mentioned above substituted C 1 -C 6 -alkoxy, ie z. B. for OCH 2 -CO-OCH 3 , OCH 2 -CO-OC 2 H 5 , OCH 2 -CO-OCH 2 -C 2 H 5 , OCH 2 -CO-OCH (CH 3 ) 2 , n-butoxycarbonyl- methoxy, 1- (methoxy carbonyl) ethoxy, 2- (methoxycarbonyl) ethoxy, 2- (ethoxy carbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxy carbonyl) ethoxy, 3- (methoxycarbonyl) propoxy , 3- (ethoxy carbonyl) propoxy, 3- (n-propoxycarbonyl) propoxy, 3- (n-butoxy carbonyl) propoxy, 4- (methoxycarbonyl) butoxy, 4- (ethoxy carbonyl) butoxy, 4- (n-propoxycarbonyl) butoxy, 4- (n-butoxy carbonyl) butoxy, 5- (methoxycarbonyl) pentoxy, 5- (ethoxy carbonyl) pentoxy, 5- (n-propoxycarbonyl) pentoxy, 5- (n-butoxy carbonyl) butoxy, 6- (methoxycarbonyl ) hexoxy, 6- (ethoxy carbonyl) hexoxy, 6- (n-propoxycarbonyl) hexoxy or 6- (n-butoxycarbonyl) hexoxy, in particular for OCH 2 -CO-OCH 3 or 1- (methoxycarbonyl) ethoxy;
- (C 1 -C 6 alkoxy) carbonyl C 1 -C 6 alkyl for: by (C 1 -C 6 alkoxy) carbonyl as mentioned above substituted C 1 -C 6 alkyl, ie z. B. for methoxycarbonylmethyl, ethoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 4 (meth oxycarbonyl) butyl, 5- (methoxycarbonyl) pentyl or 6 - (methoxy carbonyl) hexyl;
- (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 alkylsulfonyl for: by (C 1 -C 6 alkoxy) carbonyl as mentioned above substituted C 1 -C 6 alkyl, ie z. For methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1- (methoxycarbonyl) ethyl sulfonyl, 2- (methoxycarbonyl) ethylsulfonyl, 2- (ethoxy carbonyl) ethylsulfonyl, 3- (methoxycarbonyl) propylsulfonyl, 4- (methoxycarbonyl) butylsulfonyl, 5- (methoxycarbonyl) sulfonyl or 6- (methoxycarbonyl) hexylsulfonyl;
- C 1 -C 6 -Alkylthio-C 1 -C 6 -alkyl for: C 1 -C 6 -alkylthio substituted as above-mentioned C 1 -C 6 -alkyl, that is, for. B. for CH 2 -SCH 3 , CH 2 -SC 2 H 5 , n-propylthiomethyl, CH 2 -SCH (CH 3 ) 2 , n-butylthiomethyl, (1-methylpropylthio) methyl, CH 2 -SCH 2 -CH ( CH 3 ) 2 , CH 2 -SC (CH 3 ) 3 , 2-methylthioethyl, 2-ethylthioethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl , 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1,2-dimethylethylthio) ethyl, 2- (methylthio) propyl, 3- (methylthio) propyl, 2- (ethylthio) propyl , 3- (ethylthio) propyl, 3- (propylthio) propyl, 3- (butylthio) propyl, 4- (methylthio) butyl, 4- (ethylthio) butyl, 4- (n-propylthio) butyl or 4- (n -Butylthio) butyl, especially for 2- (methylthio) ethyl;
C 1 -C 6 -alkylthio- (C 1 -C 6 -alkyl) carbonyl for: by C 1 -C 6 -alkyl 58244 00070 552 001000280000000200012000285915813300040 0002019924805 00004 58125 thio as mentioned above, preferably SCH 3 or SC 2 H 5 , substituted (C 1 -C 6 alkyl) carbonyl, e.g. For methyl thiomethyl carbonyl, ethyl thiomethyl carbonyl, 1- (methyl thio) ethyl carbonyl, 2- (methyl thio) ethyl carbonyl, 3- (methyl thio) propyl carbonyl, 4- (methyl thio) butyl carbonyl, 5 (methyl thio) pentyl carbonyl or 6- (methyl thio) hexylcarbonyl, especially for CO-CH 2 -SCH 3 or CO-CH (CH 3 ) -SCH 3 ;
- Di- (C 1 -C 6 -alkyl) amino-C 1 -C 6 -alkoxy: by di- (C 1 -C 6 -alkyl) - amino such as N (CH 3 ) 2 , N (C 2 H 5 ) 2 , N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2nd -methylpropyl) amino, N [C (CH 3 ) 3 ] 2 , N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N -methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino , N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) amino, N -Ethyl-N- (1, 1-dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2nd -Methylpropyl) -N- propylamino, N- (1, 1-dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino, N- (1-methylethyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methyl propyl) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1,1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methyl propyl) amino, N- (1,1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1,1-dimethylethyl) -N- (2-methylpropyl) amino, preferably N, N-dimethylamino or N, N- Diethylamino, substituted C 1 -C 6 alkoxy, e.g. B. for OCH 2 -N (CH 3 ) 2 , OCH 2 -N (C 2 H 5 ) 2 , OCH (CH 3 ) -N (CH 3 ) 2 , 2- (dimethylamino) ethoxy, OCH (CH 3 ) -N (C 2 H 5 ) 2 , 3- (dimethylamino) propoxy, 4- (dimethylamino) butoxy, 5- (dimethylamino) pentoxy or 6- (dimethylamino) hexoxy, especially for OCH 2 -N (CH 3 ) 2 or OCH (CHj) -N (CH 3 ) 2 ;
- C 3 -C 6 alkenyl for: e.g. B. Prop-2-en-1-yl, n-buten-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, 2- Buten-1-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-2-en-1-yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl-but-3-ene - 1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl-prop-2-en-1-yl , n-Hex-3-en-1-yl, n-Hex-4-en-1-yl, n-Hex-5-en-1-yl, 1-methyl-pent-3-en-1-yl , 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4 -en-1-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1-yl, 1 , 1-Dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-2-en-1-yl, 1,2 -Dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl -but-3-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl-but -2-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-2-en-1-yl , 2-ethyl-but-3-en-1-yl, 1,1,2-trimethyl-p rop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl or 1-ethyl-2-methyl prop-2-en-1-yl, especially for prop-2 -en-1-yl or n-butene-4-yl;
- C 2 -C 6 alkenyl for: ethenyl or one of the radicals mentioned under C 3 -C 6 alkenyl, in particular for ethenyl or prop-2-en-1-yl;
- C 3 -C 6 haloalkenyl for: C 3 -C 6 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, that is, for. B. 2-chloroallyl, 3-chloroallyl, 2,3-dichlorallyl, 3,3-dichloroallyl, 2,3,3-tri chloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2 , 3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 2-chloroallyl or 3,3-dichlorallyl;
- Phenyl-C 3 -C 6 -alkenyloxy for: e.g. B. 3-phenylallyloxy, 4-phenylbut-2-enyloxy, 4-phenylbut-3-enyloxy or 5-phenylpent-4-enyloxy, preferably 3-phenylallyloxy or 4-phenylbut-2-enyloxy, especially for 3-phenylallyloxy;
- Heterocyclyl-C 3 -C 6 -alkenyloxy for: e.g. B. 3-heterocyclyl-allyl oxy, 4-heterocyclyl-but-2-enyloxy, 4-heterocyclyl-but-3-enyloxy or 5-heterocyclyl-pent-4-enyloxy, preferably 3-heterocyclyl-allyloxy or 4-heterocyclyl- but-2-enyloxy, especially for 3-heterocyclyl allyloxy;
C 3 -C 6 alkenyloxy for: prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1-yloxy, 2 -Methyl prop-2-en-1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but- 1-en-1-yl oxy, 2-methyl-but-1-en-1-yloxy, 3-methyl-but-1-en-1-yloxy, 1-methyl-but-2-en-1-yloxy , 2-methyl-but-2-en-1-yloxy, 3-methyl-but-2-en-1-yloxy, 1-methyl-but-3-en-1-yloxy, 2-methyl-but-3 -en-1-yloxy, 3-methyl-but-3-en-1-yloxy, 1,1-dimethyl-prop-2-en-1-yloxy, 1,2-dimethyl-prop-1-en-1 -yl oxy, 1,2-dimethyl-prop-2-en-1-yloxy, 1-ethyl-prop-1-en-2-yloxy, 1-ethyl-prop-2-en-1-yloxy, n -Hex-1-en-1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex -5-en-1-yloxy, 1-methyl-pent-1-en-1-yloxy, 2-methyl-pent-1-en-1-yloxy, 3-methyl-pent-1-en-1-yloxy , 4-methyl-pent-1-en-1-yl oxy, 1-methyl-pent-2-en-1-yloxy, 2-methyl-pent-2-en-1-yloxy, 3-methyl-p ent-2-en-1-yloxy, 4-methyl-pent-2-en-1-yloxy, 1-methyl-pent-3-en-1-yloxy, 2-methyl-pent-3-en-1- yloxy, 3-methyl-pent-3-en-1-yloxy, 4-methyl-pent-3-en-1-yloxy, 1-methyl-pent-4-en-1-yloxy, 2-methyl-pent- 4-en-1-yloxy, 3-methyl-pent-4-en-1-yloxy, 4-methyl-pent-4-en-1-yloxy, 1,1-dimethyl-but-2-en-1- yloxy, 1,1-dimethyl-but-3-en-1-yloxy, 1,2-dimethyl-but-1-en-1-yloxy, 1,2-dimethyl-but-2-en-1-yloxy, 1,2-dimethyl-but-3-en-1-yloxy, 1,3-dimethyl-but-1-en-1-yloxy, 1,3-dimethyl-but-2-en-1-yloxy, 1, 3-dimethyl-but-3-en-1-yloxy, 2,2-dimethyl-but-3-en-1-yloxy, 2,3-dimethyl-but-1-en-1-yloxy, 2,3- Dimethyl-but-2-en-1-yloxy, 2,3-dimethyl-but-3-en-1-yloxy, 3,3-dimethyl-but-1-en-1-yloxy, 3,3-dimethyl but-2-en-1-yloxy, 1-ethyl-but-1-en-1-yloxy, 1-ethyl-but-2-en-1-yloxy, 1-ethyl-but-3-en-1- yloxy, 2-ethyl-but-1-en-1-yloxy, 2-ethyl-but-2-en-1-yloxy, 2-ethyl-but-3-en-1-yloxy, 1,1,2- Trimethyl-prop-2-en-1-yloxy, 1-ethyl-1-methyl-prop-2-en-1-yloxy, 1-ethyl-2-methyl-prop-1-en-1-yloxy or 1- Ethyl 2-methyl-prop-2-e n-1-yloxy, especially for prop-2-en-1-yloxy;
- C 2 -C 6 alkenyloxy for: ethenyloxy or one of the radicals mentioned under C 3 -C 6 alkenyloxy, in particular for ethenyloxy or prop-2-en-1-yloxy;
- C 3 -C 6 haloalkenyloxy for: C 3 -C 6 alkenyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, that is, for. B. 2-chloroallyloxy, 3-chloroallyloxy, 2,3-dichloroallyloxy, 3,3-dichloroallyloxy, 2,3,3-trichloroallyloxy, 2,3-dichlorobut-2-enyloxy, 2-bromo allyloxy, 3-bromoallyloxy, 2 , 3-dibromoallyloxy, 3,3-dibromo allyloxy, 2,3,3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular for 2-chloroallyloxy or 3,3-dichloroallyloxy;
C 3 -C 6 alkenylthio for: prop-1-en-1-ylthio, prop-2-en-1-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2-ylthio, n-buten-3-ylthio, 1-methyl-prop-1-en-1-ylthio, 2-methyl-prop-1-en-1-ylthio, 1-methyl-prop-2-en-1-ylthio, 2 -Methyl prop-2-en-1-ylthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1-methyl-but- 1-en-1-ylthio, 2-methyl-but-1-en-1-ylthio, 3-methyl-but-1-en-1-ylthio, 1-methyl-but-2-en-1-ylthio, 2-methyl-but-2-en-1-ylthio, 3-methyl-but-2-en-1-ylthio, 1-methyl-but-3-en-1-ylthio, 2-methyl-but-3- en-1-ylthio, 3-methyl-but-3-en-1-ylthio, 1,1-dimethyl-prop-2-en-1-ylthio, 1,2-dimethyl-prop-1-en-1- ylthio, 1,2-dimethyl-prop-2-en-1-ylthio, 1-ethyl-prop-1-en-2-ylthio, 1-ethyl-prop-2-en-1-ylthio, n-hex 1-en-1-ylthio, n-hex-2-en-1-ylthio, n-hex-3-en-1-ylthio, n-hex-4-en-1-ylthio, n-hex-5- en-1-ylthio, 1-methyl-pent-1-en-1-ylthio, 2-methyl-pent-1-en-1-ylthio, 3-methyl-pent-1-en-1-ylthio, 4- Methyl-pent-1-en-1-ylthio, 1-methyl-pent-2-en-1-ylthi o, 2-methyl-pent-2-en-1-ylthio, 3-methyl-pent-2-en-1-ylthio, 4-methyl-pent-2-en-1-ylthio, 1-methyl-pent- 3-en-1-ylthio, 2-methyl-pent-3-en-1-ylthio, 3-methyl-pent-3-en-1-ylthio, 4-methyl-pent-3-en-1-ylthio, 1-methyl-pent-4-en-1-ylthio, 2-methyl-pent-4-en-1-ylthio, 3-methyl-pent-4-en-1-ylthio, 4-methyl-pent-4- en-1-ylthio, 1,1-dimethyl-but-2-en-1-ylthio, 1,1-dimethyl-but-3-en-1-ylthio, 1,2-dimethyl-but-1-en- 1-ylthio, 1,2-dimethyl-but-2-en-1-ylthio, 1,2-dimethyl-but-3-en-1-ylthio, 1,3-dimethyl-but-1-en-1- ylthio, 1,3-dimethylbut-2-en-1-ylthio, 1,3-dimethylbut-3-en-1-ylthio, 2,2-dimethylbut-3-en-1-ylthio, 2,3-dimethyl-but-1-en-1-ylthio, 2,3-dimethyl-but-2-en-1-ylthio, 2,3-dimethyl-but-3-en-1-ylthio, 3, 3-dimethyl-but-1-en-1-ylthio, 3,3-dimethyl-but-2-en-1-ylthio, 1-ethyl-but-1-en-1-ylthio, 1-ethyl-but- 2-en-1-ylthio, 1-ethyl-but-3-en-1-ylthio, 2-ethyl-but-1-en-1-ylthio, 2-ethyl-but-2-en-1-ylthio, 2-ethyl-but-3-en-1-ylthio, 1,1,2-trimethyl-prop-2-en-1-ylthio, 1-ethyl-1-methyl prop-2-ene -1-ylthio, 1-ethyl-2-methyl-prop-1-en-1-ylthio or 1-ethyl-2-methyl-prop-2-en-1-ylthio, especially for prop-2-en-1 -ylthio;
- C 2 -C 6 alkenylthio for: ethenylthio or one of the radicals mentioned under C 3 -C 6 alkenylthio, in particular for ethenyl thio or prop-2-en-1-ylthio;
- C 3 -C 6 alkynyl for: prop -1-in-1-yl, prop-2-in-1-yl, n-but-1-in-1-yl, n-but-1-yl 3-yl, n-but-1-in-4-yl, n-but-2-in-1-yl, n-pent-1-in-1-yl, n-pent-1-in-3- yl, n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n-pent-2-in-5-yl, 3-methyl-but-1-in-3-yl, 3-methyl-but-1-in-4-yl, n-hex-1-in-1- yl, n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n-hex-1-in-6-yl, n-hex-2-in-1-yl, n-hex-2-in-4-yl, n-hex-2-in-5-yl, n-hex-2-in-6-yl., n -Hex-3-in-1-yl, n-hex-3-in-2-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-3-yl , 3-methylpent-1-in-4-yl, 3-methylpent-1-in-5-yl, 4-methylpent-1-in-1-yl, 4-methylpent-2 -in-4-yl or 4-methyl-pent-2-in-5-yl, in particular for prop-2-in-1-yl;
- C 2 -C 6 alkynyl for: ethynyl or one of the radicals mentioned under C 3 -C 6 alkynyl, in particular for ethynyl or prop-2-yn-1-yl;
- C 3 -C 6 alkynyloxy for: prop-1-in-1-yloxy, prop-2-in-1-yloxy, n-but-1-in-1-yloxy, n-but-1-in 3-yloxy, n-but-1-in-4-yloxy, n-but-2-in-1-yloxy, n-pent-1-in-1-yloxy, n-pent-1-in-3- yloxy, n-pent-1-in-4-yloxy, n-pent-1-in-5-yloxy, n-pent-2-in-1-yl oxy, n-pent-2-in-4-yloxy , n-Pent-2-in-5-yloxy, 3-methyl-but-1-in-3-yloxy, 3-methyl-but-1-in-4-yloxy, n-hex-1-in-1 -yl oxy, n-Hex-1-in-3-yloxy, n-Hex-1-in-4-yloxy, n-Hex-1-in-5-yl oxy, n-Hex-1-in-6 -yloxy, n-Hex-2-in-1-yloxy, n-Hex-2-in-4-yl oxy, n-Hex-2-in-5-yloxy, n-Hex-2-in-6- yloxy, n-hex-3-in-1-yloxy, n-hex-3-in-2-yloxy, 3-methylpent-1-in-1-yloxy, 3-methylpent-1-in-3 -yloxy, 3-methyl-pent-1-in-4-yloxy, 3-methyl-pent-1-in-5-yloxy, 4-methyl-pent-1-in-1-yloxy, 4-methyl-pent -2-in-4-yloxy or 4-methylpent-2-in-5-yloxy, especially for prop-2-in-1-yloxy;
- C 2 -C 6 alkynyloxy for: ethynyloxy or one of the radicals mentioned under C 3 -C 6 -alkynyloxy, in particular for ethynyloxy or prop-2-yn-1-yloxy;
C 3 -C 6 alkynylthio for: prop-1-in-1-ylthio, prop-2-in-1-ylthio, n-but-1-in-1-ylthio, n-but-1-in 3-ylthio, n-but-1-in-4-ylthio, n-but-2-in-1-ylthio, n-pent-1-in-1-ylthio, n-pent-1-in-3- ylthio, n-pent-1-in-4-ylthio, n-pent-1-in-5-ylthio, n-pent-2-in-1-ylthio, n-pent-2-in-4-ylthio, n-pent-2-in-5-ylthio, 3-methyl-but-1-in-3-ylthio, 3-methylbut-1-in-4-ylthio, n-hex-1-in-1-ylthio, n-hex-1-in-3-ylthio, n-hex-1-in-4-ylthio, n-hex-1-in-5-ylthio, n-hex-1-in-6-ylthio, n- Hex-2-in-1-ylthio, n-hex-2-in-4-ylthio, n-hex-2-in-5-ylthio, n-hex-2-in-6-ylthio, n-hex 3-in-1-ylthio, n-hex-3-in-2-ylthio, 3-methylpent-1-in-1-ylthio, 3-methylpent-1-in-3-ylthio, 3-methyl- pent-1-in-4-ylthio, 3-methylpent-1-in-5-ylthio, 4-methyl-pent-1-in-1-ylthio, 4-methyl-pent-2-in-4-ylthio or 4-methyl-pent-2-in-5-ylthio, especially for prop-2-in-1-ylthio;
- C 2 -C 6 alkynylthio for: ethynylthio or one of the radicals mentioned under C 3 -C 6 -alkynylthio, in particular for ethynylthio or prop-2-ynthio;
- (C 3 -C 6 alkenyl) oxycarbonyl for: prop-1-en-1-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2 -yloxycarbonyl, n-buten-3-yloxycarbonyl, 1-methyl-prop-1-en-1-yloxycarbonyl, 2-methyl-prop-1-en-1-yloxycarbonyl, 1-methyl-prop-2-en-1 -yloxy carbonyl, 2-methyl-prop-2-en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl , 1-methyl-but-1-en-1-yloxycarbonyl, 2-methyl-but-1-en-1-yloxycarbonyl, 3-methyl-but-1-en-1-yloxycarbonyl, 1-methyl-but-2 -en-1-yloxycarbonyl, 2-methyl-but-2-en-1-yloxycarbonyl, 3-methyl-but-2-en-1-yloxy carbonyl, 1-methyl-but-3-en-1-yloxycarbonyl, 2-methyl-but-3-en-1-yloxycarbonyl, 3-methyl-but-3-en-1-yloxycarbonyl, 1, 1-dimethyl-prop-2-en-1-yloxycarbonyl, 1,2-dimethyl- prop-1- en-1-yloxycarbonyl, 1,2-dimethyl-prop-2-en-1-yloxycarbonyl, 1-ethyl-prop-1-en-2-yloxycarbonyl, 1-ethyl-prop-2-en- 1-yloxy carbonyl, n-hex-1-en-1-yloxycarbonyl, n-hex-2-en- 1-yloxy carbonyl, n-hex-3-en-1-yloxycarbonyl, n-hex-4-en-1-yloxy carbonyl, n-hex-5-en-1-yloxycarbony1, 1-methyl-pent-1- en-1-yloxycarbonyl, 2-methyl-pent-1-en-1-yloxycarbonyl, 3-methyl-pent-1-en-1-yloxycarbonyl, 4-methyl-pent-1-en-1-yloxycarbonyl, 1 -Methyl-pent-2-en-1-yloxycarbonyl, 2-methyl-pent-2-en-1-yloxycarbonyl, 3-methyl-pent-2-en-1-yloxycarbonyl, 4-methyl-pent-2-ene -1-yloxycarbonyl, 1-methyl-pent-3-en-1-yloxycarbonyl, 2-methyl-pent-3-en-1-yloxycarbonyl, 3-methyl-pent-3-en-1-yloxycarbonyl, 4-methyl -pent-3-en-1-yloxycarbonyl, 1-methyl-pent-4-en-1-yloxycarbonyl, 2-methyl-pent-4-en-1-yloxycarbonyl, 3-methyl-pent-4-en- 1-yloxycarbonyl, 4-methyl-pent-4-en-1-yloxycarbonyl, 1,1-dimethyl-but-2-en-1-yloxycarbonyl, 1,1-dimethyl-but-3-en-1-yloxycarbonyl, 1,2-dimethyl-but-1-en-1-yloxycarbonyl, 1,2-dimethyl-but-2-en-1-yloxycarbonyl, 1,2-dimethyl-but-3-en-1-yloxycarbonyl, 1 , 3-dimethyl-but-1-en-1-yloxycarbonyl, 1,3-dimethyl-but-2-en-1-yloxycarbonyl, 1,3-dimethyl-but-3-en-1-yloxycarbonyl yl, 2,2-dimethyl-but-3-en-1-yloxycarbonyl, 2,3-dimethyl-but-1-en-1-yloxycarbonyl, 2,3-dimethyl-but-2-en-1-yloxycarbonyl , 2,3-dimethyl-but-3-en-1-yloxycarbonyl, 3,3-dimethyl-but-1-en-1-yloxycarbonyl, 3,3-dimethyl-but-2-en-1-yloxycarbonyl, 1-ethyl-but-1-en-1-yloxycarbonyl, 1-ethyl-but-2-en-1-yloxycarbonyl, 1-ethyl-but-3-en-1-yloxycarbonyl, 2-ethyl-but-1 - en-1-yloxycarbonyl, 2-ethyl-but-2-en-1-yloxycarbonyl, 2-ethyl-but-3-en-1-yloxycarbonyl, 1,1,2-trimethyl-prop-2-en-1 -yloxycarbonyl, 1-ethyl-1-methyl-prop-2-en-1-yloxycarbonyl, 1-ethyl-2-methyl-prop-1-en-1-yloxycarbonyl or 1-ethyl-2-methyl-prop-2 -en-1-yloxycarbonyl, especially for prop-2-en-1-yloxycarbonyl;
- (C 3 -C 6 alkenyloxy) carbonyl-C 1 -C 6 alkyl for: by (C 3 -C 6 alkenyloxy) carbonyl as mentioned above, preferably prop-2-en-1-yl-oxycarbonyl, substituted C 1 -C 6 alkyl, for example prop-2-en-1-yl-oxycarbonyl-methyl;
- (C 3 -C 6 alkenyl) carbonyloxy for: prop-1-en-1-ylcarbonyloxy, prop-2-en-1-ylcarbonyloxy, 1-methylethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n-buten-2 -ylcarbonyloxy, n-butene-3-ylcarbonyloxy, 1-methyl-prop-1-en-1-ylcarbonyloxy, 2-methyl-prop-1-en-1-ylcarbonyloxy, 1-methyl-prop-2-en-1 -yl-carbonyloxy, 2-methyl-prop-2-en-1-ylcarbonyloxy, n-penten-1-ylcarbonyloxy, n-penten-2-ylcarbonyloxy, n-penten-3-ylcarbonyloxy, n-penten-4 -ylcarbonyloxy, 1-methyl-but-1-en-1-ylcarbonyloxy, 2-methyl-but-1-en-1-ylcarbonyloxy, 3-methyl but-1-en-1-ylcarbonyloxy, 1-methyl-but- 2-en-1-ylcarbonyloxy, 2-methyl-but-2-en-1-ylcarbonyloxy, 3-methyl-but-2-en-1-yl carbonyloxy, 1-methyl-but-3-en-1-ylcarbonyloxy , 2-methylbut-3-en-1-ylcarbonyloxy, 3-methylbut-3-en-1-ylcarbonyloxy, 1,1-dimethyl-prop-2-en-1-ylcarbonyloxy, 1,2-dimethyl prop-1 en-1-ylcarbonyloxy, 1,2-dimethyl-prop-2-en-1-ylcarbonyloxy, 1-ethyl-prop-1-en-2-ylcarbonyloxy, 1-ethyl-prop-2-en-1 -yl carbonyloxy, n-hex-1-en-1-ylcarbonyloxy, n-hex-2-en-1-y l carbonyloxy, n-hex-3-en-1-ylcarbonyloxy, n-hex-4-en-1-yl carbonyloxy, n-hex-5-en-1-ylcarbonyloxy, 1-methyl-pent-1-en- 1-ylcarbonyloxy, 2-methyl-pent-1-en-1-ylcarbonyloxy, 3-methyl-pent-1-en-1-ylcarbonyloxy, 4-methyl-pent-1-en-1-yl carbonyloxy, 1-methyl -pent-2-en-1-ylcarbonyloxy, 2-methyl-pent-2-en-1-ylcarbonyloxy, 3-methyl-pent-2-en-1-ylcarbonyloxy, 4-methyl-pent-2-en- 1-ylcarbonyloxy, 1-methyl-pent-3-en-1-ylcarbonyloxy, 2-methyl-pent-3-en-1-ylcarbonyloxy, 3-methyl-pent-3-en-1-ylcarbonyloxy, 4-methyl- pent-3-en-1-yl carbonyloxy, 1-methyl-pent-4-en-1-ylcarbonyloxy, 2-methyl-pent-4-en-1-ylcarbonyloxy, 3-methyl-pent-4-en-1 -ylcarbonyl oxy, 4-methyl-pent-4-en-1-ylcarbonyloxy, 1, 1-dimethyl-but-2-en-1-ylcarbonyloxy, 1, 1-dimethyl-but-3-en-1-ylcarbonyloxy, 1,2-dimethyl-but-1-en-1-ylcarbonyloxy, 1,2-dimethyl-but-2-en-1-ylcarbonyloxy, 1,2-dimethyl-but-3-en-1-ylcarbonyloxy, 1, 3-dimethyl-but-1-en-1-ylcarbonyloxy, 1,3-dimethyl-but-2-en-1-ylcarbonyloxy, 1,3-dimethyl-but-3-en-1-ylcarbonyloxy, 2,2-dimethyl-but-3-en-1-ylcarbonyloxy, 2,3-dimethyl-but-1-en-1-ylcarbonyloxy, 2,3-dimethyl-but-2-en-1-ylcarbonyloxy, 2, 3-dimethyl-but-3-en-1-ylcarbonyloxy, 3,3-dimethyl-but-1-en-1-ylcarbonyloxy, 3,3-dimethyl-but-2-en-1-ylcarbonyloxy, 1-ethyl- but-1-en-1-ylcarbonyloxy, 1-ethyl-but-2-en-1-yl carbonyloxy, 1-ethyl-but-3-en-1-ylcarbonyloxy, 2-ethyl-but-1-en-1 -ylcarbonyloxy, 2-ethyl-but-2-en-1-ylcarbonyloxy, 2-ethyl-but-3-en-1-ylcarbonyloxy, 1,1,2-trimethyl-prop-2-en-1-ylcarbonyloxy, 1 -Ethyl-1-methyl-prop-2-en-1-ylcarbonyloxy, 1-ethyl-2-methyl-prop-1-en-1-ylcarbonyloxy or 1-ethyl-2-methyl-prop-2-en- 1-ylcarbonyloxy, especially for prop-2-en-1-ylcarbonyloxy;
- (C 2 -C 6 alkenyl) carbonyloxy for: ethenylcarbonyloxy or one of the radicals mentioned under (C 3 -C 6 alkenyl) carbonyloxy, in particular for ethenylcarbonyloxy or prop-2-en-1-yl carbonyloxy;
- (C 3 -C 6 alkenyl) carbonylthio for: prop-1-en-1-ylcarbonylthio, prop-2-en-1-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n-butene-2 -ylcarbonylthio, n-butene-3-ylcarbonylthio, 1-methyl-prop-1-en-1-ylcarbonylthio, 2-methyl-prop-1-en-1-ylcarbonylthio, 1-methyl-prop-2-en-1 -yl carbonylthio, 2-methyl-prop-2-en-1-ylcarbonylthio, n-penten-1-ylcarbonylthio, n-penten-2-ylcarbonylthio, n-penten-3-yl carbonylthio, n-penten-4-ylcarbonylthio , 1-methyl-but-1-en-1-ylcarbonylthio, 2-methyl-but-1-en-1-ylcarbonylthio, 3-methyl-but-1-en-1-ylcarbonylthio, 1-methyl-but-2 -en-1-yl carbonylthio, 2-methyl-but-2-en-1-ylcarbonylthio, 3-methyl-but-2-en-1-ylcarbonylthio, 1-methyl-but-3-en-1-ylcarbonylthio , 2-methyl-but-3-en-1-ylcarbonylthio, 3-methyl-but-3-en-1-ylcarbonylthio, 1,1-dimethyl-prop-2-en-1-ylcarbonylthio, 1,2-dimethyl -prop-1-en-1-ylcarbonylthio, 1,2-dimethyl-prop-2-en-1-ylcarbonylthio, 1-ethyl-prop-1-en-2-ylcarbonylthio, 1-ethyl-prop-2-ene -1-ylcarbonylthio, n-hex-1-en-1 -ylcarbonylthio, n-Hex-2-en-1-ylcarbonylthio, n-Hex-3-en-1-ylcarbonylthio, n-Hex-4-en-1-ylcarbonylthio, n-Hex-5-en-1 -ylcarbonylthio, 1-methyl-pent-1-en-1-ylcarbonylthio, 2-methyl-pent-1-en-1-ylcarbonylthio, 3-methyl-pent-1-en-1-ylcarbonylthio, 4-methyl- pent-1-en-1-ylcarbonylthio, 1-methyl-pent-2-en-1-yl carbonylthio, 2-methyl-pent-2-en-1-ylcarbonylthio, 3-methyl-pent-2-en-1 -ylcarbonylthio, 4-methyl-pent-2-en-1-ylcarbonylthio, 1-methyl-pent-3-en-1-ylcarbonylthio, 2-methyl-pent-3-en-1-ylcarbonylthio, 3-methyl- pent-3-en-1-ylcarbonylthio, 4-methyl-pent-3-en-1-ylcarbonylthio, 1-methyl-pent-4-en-1-yl carbonylthio, 2-methyl-pent-4-en-1 -ylcarbonylthio, 3-methyl-pent-4-en-1-ylcarbonylthio, 4-methyl-pent-4-en-1-ylcarbonylthio, 1,1-dimethyl-but-2-en-1-ylcarbonylthio, 1, 1-dimethylbut-3-en-1-ylcarbonylthio, 1,2-dimethylbut-1-en-1-yl carbonylthio, 1,2-dimethylbut-2-en-1-ylcarbonylthio, 1,2- Di methyl-but-3-en-1-ylcarbonylthio, 1,3-dimethyl-but-1-en-1-yl carbonylthio, 1,3-dimethyl-but-2-ene -1-ylcarbonylthio, 1,3-dimethyl-but-3-en-1-ylcarbonylthio, 2,2-dimethyl-but-3-en-1-yl carbonylthio, 2,3-dimethyl-but-1-ene -1-ylcarbonylthio, 2,3-dimethyl-but-2-en-1-ylcarbonylthio, 2,3-dimethyl-but-3-en-1-yl carbonylthio, 3,3-dimethyl-but-1-ene -1-ylcarbonylthio, 3,3-dimethyl-but-2-en-1-ylcarbonylthio, 1-ethyl-but-1-en-1-yl carbonylthio, 1-ethyl-but-2-en-1-ylcarbonylthio , 1-ethyl-but-3-en-1-ylcarbonylthio, 2-ethyl-but-1-en-1-ylcarbonylthio, 2-ethyl-but-2-en-1-ylcarbonylthio, 2-ethyl-but-3 -en-1-yl carbonylthio, 1, 1,2-trimethyl-prop-2-en-1-ylcarbonylthio, 1-ethyl-1-methyl-prop-2-en-1-ylcarbonylthio, 1-ethyl-2- methyl-prop-1-en-1-ylcarbonylthio or 1-ethyl-2-methyl-prop-2-en-1-ylcarbonylthio, in particular for prop-2-en-1-yl carbonylthio;
- (C 2 -C 6 -Alkenyl) carbonylthio for: ethenylcarbonylthio or one of the radicals mentioned under (C 3 -C 6 -alkenyl) carbonylthio, in particular for prop-2-en-1-ylcarbonylthio;
- (C 3 -C 6 alkynyl) carbonyloxy for: prop-1-in-1-ylcarbonyloxy, prop-2-in-1-ylcarbonyloxy, n-but-1-in-1-ylcarbonyloxy, n-but-1 -in-3-ylcarbonyloxy, n-but-1-in-4-ylcarbonyloxy, n-but-2-in-1-ylcarbonyloxy, n-pent-1-in-1-ylcarbonyloxy, n-pent-1-in -3-ylcarbonyloxy, n-pent-1-in-4-ylcarbonyloxy, n-pent-1-in-5-ylcarbonyloxy, n-pent-2-in-1-ylcarbonyloxy, n-pent-2-in-4 -ylcarbonyloxy, n-pent-2-in-5-ylcarbonyloxy, 3-methyl-but-1-in-3-ylcarbonyloxy, 3-methyl-but-1-in-4-yl carbonyloxy, n-hex-1- in-1-ylcarbonyloxy, n-hex-1-in-3-yl carbonyloxy, n-hex-1-in-4-ylcarbonyloxy, n-hex-1-in-5-yl carbonyloxy, n-hex-1- in-6-ylcarbonyloxy, n-Hex-2-in-1-yl carbonyloxy, n-Hex-2-in-4-ylcarbonyloxy, n-Hex-2-in-5-yl carbonyloxy, n-Hex-2- in-6-ylcarbonyloxy, n-hex-3-in-1-yl carbonyloxy, n-hex-3-in-2-ylcarbonyloxy, 3-methylpent-1-in-1-ylcarbonyloxy, 3-methyl-pent-1 -in-3-ylcarbonyloxy, 3-methyl-pent-1-in-4-ylcarbonyloxy, 3-methyl-pent-1-in-5-yl carbonyloxy, 4-methyl-pent-1-in-1-ylcarbonyloxy, 4-methylpent-2-yn-4-ylcar bonyloxy or 4-methylpent-2-in-5-yl carbonyloxy, especially for prop-2-in-1-ylcarbonyloxy;
- (C 2 -C 6 -alkynyl) carbonyloxy for: ethynylcarbonyloxy or one of the radicals mentioned under (C 3 -C 6 -alkynyl) carbonyloxy, in particular for ethynylcarbonyloxy or prop-2-in-1-ylcarbonyloxy;
- C 3 -C 6 alkynylsulfonyloxy for: prop-1-in-1-ylsulfonyloxy, prop-2-in-1-ylsulfonyloxy, n-but-1-in-1-ylsulfonyloxy, n-but-1-in- 3-ylsulfonyloxy, n-but-1-in-4-ylsulfonyloxy, n-but-2-in-1-ylsulfonyloxy, n-pent-1-in-1-ylsulfonyloxy, n-pent-1-in-3- ylsulfonyloxy, n-pent-1-in-4-ylsulfonyloxy, n-pent-1-in-5-ylsulfonyloxy, n-pent-2-in-1-ylsulfonyloxy, n-pent-2-in-4-ylsulfonyloxy, n-pent-2-in-5-ylsulfonyloxy, 3-methyl-but-1-in-3-ylsulfonyloxy, 3-methyl-but-1-in-4-yl sulfonyloxy, n-hex-1-in-1 -ylsulfonyloxy, n-Hex-1-in-3-yl sulfonyloxy, n-Hex-1-in-4-ylsulfonyloxy, n-Hex-1-in-5-yl sulfonyloxy, n-Hex-1-in-6 -ylsulfonyloxy, n-Hex-2-in-1-yl sulfonyloxy, n-Hex-2-in-4-ylsulfonyloxy, n-Hex-2-in-5-yl sulfonyloxy, n-Hex-2-in-6 -ylsulfonyloxy, n-Hex-3-in-1-yl sulfonyloxy, n-Hex-3-in-2-ylsulfonyloxy, 3-Methylpent-1- in-1-ylsulfonyloxy, 3-Methyl-pent-1-in- 3-ylsulfonyloxy, 3-methyl-pent-1-in-4-ylsulfonyloxy, 3-methyl-pent-1-in-5-yl sulfonyloxy, 4-methyl-pent-1-in-1-ylsulfonyloxy, 4-methyl pent-2-in-4-ylsulfo nyloxy or 4-methylpent-2-in-5-yl sulfonyloxy, especially for prop-2-in-1-ylsulfonyloxy;
- (C 3 -C 6 alkynyl) carbonylthio for: prop-1-in-1-ylcarbonylthio, prop-2-in-1-ylcarbonylthio, n-but-1-in-1-ylcarbonylthio, n-but-1 -in-3-ylcarbonylthio, n-but-1-in-4-ylcarbonylthio, n-but-2-in-1-ylcarbonylthio, n-pent-1-in-1-ylcarbonylthio, n-pent-1-in -3-ylcarbonylthio, n-pent-1-in-4-ylcarbonylthio, n-pent-1-in-5-ylcarbonylthio, n-pent-2-in-1-ylcarbonylthio, n-pent-2-in-4 -ylcarbonylthio, n-pent-2-in-5-ylcarbonylthio, 3-methyl-but-1-in-3-ylcarbonylthio, 3-methylbut-1-in-4-yl carbonylthio, n-hex-1-in- 1-ylcarbonylthio, n-hex-1-in-3-yl carbonylthio, n-hex-1-in-4-ylcarbonylthio, n-hex-1-in-5-yl carbonylthio, n-hex-1-in- 6-ylcarbonylthio, n-Hex-2-in-1-yl carbonylthio, n-Hex-2-in-4-ylcarbonylthio, n-Hex-2-in-5-yl carbonylthio, n-Hex-2-in- 6-ylcarbonylthio, n-hex-3-in-1-yl carbonylthio, n-hex-3-in-2-ylcarbonylthio, 3-methylpent-1-in-1-ylcarbonylthio, 3-methyl-pent-1-in -3-ylcarbonylthio, 3-methyl-pent-1-in-4-ylcarbonylthio, 3-methylpent-1-in-5-yl carbonylthio, 4-methyl-pent-1-in-1-ylcarbonylthi o, 4-methyl-pent-2-in-4-ylcarbonylthio or 4-methyl-pent-2-in-5-yl carbonylthio, in particular for prop-2-in-1-ylcarbonylthio;
- (C 2 -C 6 -Alkinyl) carbonylthio for: ethynylcarbonylthio or one of the radicals mentioned under (C 3 -C 3 -alkynyl) carbonylthio, in particular for ethynylcarbonylthio or prop-2-yn-1-yl carbonylthio;
- (C 1 -C 6 -alkoxy) carbonyl-C 2 -C 6 alkenyl of: by (C 1 -C 6 alkoxy) carbonyl as mentioned feedforward thend substituted C 2 -C 6 alkenyl, as for example, prop-methoxycarbonyl 2-en-1-yl;
- C 3 -C 6 alkenyloxy-C 1 -C 6 alkyl for: by C 3 -C 6 alkenyloxy as mentioned above, preferably allyloxy, 2-methylprop-2-en-1-yloxy, but-1 -en-3-yloxy, but-1-en-4-yloxy or but-2-en-1-yloxy substituted C 1 -C 6 alkyl, for example for allyloxymethyl, 2-allyloxyethyl or but-1-ene -4-yloxymethyl;
- C 3 -C 6 alkynyloxy-C 1 -C 6 -alkyl for: by C 3 -C 6 -alkynyloxy as mentioned above, preferably propargyloxy, but-1-yn-3-yl oxy, but-1-yl 4-yloxy or but-2-yn-1-yloxy, substituted C 1 -C 6 alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl;
- C 3 -C 7 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular for cyclopentyl or cyclohexyl;
- C 3 -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
- C 3 -Ca cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, in particular for cyclopentyl or cyclohexyl;
- C 3 -C 8 cycloalkyl-C 1 -C 4 alkyl for: cyclopropylmethyl, cyclo butylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo heptylmethyl, cyclooctylmethyl, 1- (cyclopropyl) ethyl, 1- (cyclobutyl) ethyl, 1- (cyclopentyl ) ethyl, 1- (cyclohexyl) ethyl, 1- (cycloheptyl) ethyl, 1- (cyclooctyl) ethyl, 2- (cyclopropyl) ethyl, 2- (cyclobutyl) ethyl, 2- (cyclopentyl) ethyl, 2- ( Cyclohexyl) ethyl, 2- (cycloheptyl) ethyl, 2- (cyclooctyl) ethyl, 3- (cyclopropyl) propyl, 3- (cyclo butyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl) propyl, 3- ( Cycloheptyl) propyl, 3- (cyclooctyl) propyl, 4- (cyclopropyl) butyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl, 4- (cyclohexyl) butyl, 4- (cycloheptyl) butyl or 4- ( Cyclo octyl) butyl, especially for cyclopentylmethyl or cyclo hexylmethyl;
- C 3 -C 6 cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclo pentyloxy or cyclohexyloxy;
- C 3 -C 6 cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;
- C 3 -C 6 cycloalkylcarbonyloxy for: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
- C 3 -C 6 cycloalkylsulfonyloxy for: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
- C 3 -C 6 cycloalkyloxy-C 1 -C 4 alkyl for: cyclopropyloxymethyl, cyclobutyloxymethyl, cyclopentyloxymethyl, cyclohexyloxy methyl, 1- (cyclopropyloxy) ethyl, 1- (cyclobutyloxy) ethyl, 1- (cyclopentyloxy) ethyl, 1- (Cyclohexyloxy) ethyl, 2- (cyclopropyloxy) ethyl, 2- (cyclobutyloxy) ethyl, 2- (cyclopentyl oxy) ethyl, 2- (cyclohexyloxy) ethyl, 3- (cyclopropyloxy) propyl, 3- (cyclobutyloxy) propyl, 3 - (Cyclopentyloxy) propyl, 3- (cyclohexyloxy) propyl 4- (cyclopropyloxy) butyl, 4- (cyclobutyl oxy) butyl, 4- (cyclopentyloxy) butyl or 4- (cyclohexyl oxy) butyl, especially for cyclopentyloxymethyl, cyclohexyl oxymethyl or 2- (cyclopentyloxy) ethyl;
- C 5 -C 7 cycloalkenyloxy for: cyclopent-1-enyloxy, cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclo hex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1 -enyloxy, cyclohept-2-enyloxy, cyclohept-3-enyloxy or cyclohept-4-enyloxy;
- C 1 -C 3 alkylene for: methylene, 1,2-ethylene or 1,3-propylene.

Unter 3- bis 7-gliedrigem Heterocyclyl - das direkt oder über eine Sauerstoff-, Alkoxy-, Alkenyloxy- oder Alkinyloxybrücke ver knüpft sein kann - sind sowohl gesättigte, partiell oder voll ständig ungesättigte als auch aromatische Heterocyclen mit ein bis drei Heteroatomen, ausgewählt aus einer Gruppe bestehend aus
From 3- to 7-membered heterocyclyl - which can be linked directly or via an oxygen, alkoxy, alkenyloxy or alkynyloxy bridge - both saturated, partially or completely unsaturated and aromatic heterocycles with one to three heteroatoms are selected from a group consisting of

- one to three nitrogen atoms,
- one or two oxygen and
- one or two sulfur atoms, to understand.

Im Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen der Formel I als Herbizide und/oder als defoliant/desikkant wirk same Verbindungen haben die Variablen vorzugsweise folgende Be deutungen, und zwar jeweils für sich allein oder in Kombination:
X-CH₂- oder -NH-
R₁ Methyl oder Amino, vorzugsweise Methyl
R₂ Methyl
R₃ Wasserstoff oder Halogen, insbesondere Chlor oder Brom, beson ders bevorzugt Chlor
R₄ Halogen, insbesondere Chlor oder Brom, oder C₁-C₄-Alkoxy, C₂-C₆-Alkenoxy, C₂-C₆-Alkinoxy, C₁-C₄-Alkoxycarbonyl, C₂-C₆-Al- kenoxycarbonyl, C₂-C₆-Alkinoxycarbonyl
R₅ in Position α Wasserstoff, Halogen (insbesondere Chlor) oder C₁-C₄-Alkoxy
R₆ in Position β ggf. substituiertes C₁-C₄-Alkoxy, ggf. substi tuiertes C₂-C₆-Alkenoxy, ggf substituiertes C₂-C₆-Alkinoxy, ggf. substituiertes C₁-C₄-Alkoxycarbonyl, ggf. substituiertes C₂-C₆-Alkenoxycarbonyl, ggf. substituiertes C₂-C₆-Alkinoxycar bonyl,
Nitro oder Wasserstoff (insbesondere eine Nitrogruppe).With regard to the use of the compounds of the formula I according to the invention as herbicides and / or as defoliant / desiccant compounds, the variables preferably have the following meanings, in each case individually or in combination:
X-CH ₂ - or -NH-
R _{1 is} methyl or amino, preferably methyl
R ₂ methyl
R _{3 is} hydrogen or halogen, especially chlorine or bromine, particularly preferably chlorine
R ₄ halogen, in particular chlorine or bromine, or C ₁ -C ₄ alkoxy, C ₂ -C ₆ alkenoxy, C ₂ -C ₆ alkynoxy, C ₁ -C ₄ alkoxycarbonyl, C ₂ -C ₆ -Al- kenoxycarbonyl, C ₂ -C ₆ alkynoxycarbonyl
R ₅ in position α is hydrogen, halogen (especially chlorine) or C ₁ -C ₄ alkoxy
R ₆ in position β optionally substituted C ₁ -C ₄ alkoxy, substi tuiertes C ₂ -C ₆ alkenoxy, if necessary, optionally substituted C ₂ -C ₆ alkynoxy, optionally substituted C ₁ -C ₄ alkoxycarbonyl, optionally substituted C ₂ -C ₆ alkenoxycarbonyl, optionally substituted C ₂ -C ₆ alkynoxycarbonyl,
Nitro or hydrogen (especially a nitro group).

Besonders bevorzugte Verbindungen der Formel I sind in den nach folgenden Tabellen aufgeführt. Particularly preferred compounds of formula I are in the following tables.

Tabelle 1. Verbindungen Ia (mit X = CH₂, R¹=CH₃, R²=CH₃, R³=R⁴=C¹) Table 1. Compounds Ia (with X = CH ₂ , R ¹ = CH ₃ , R ² = CH ₃ , R ³ = R ⁴ = C ¹ )

Weiterhin bevorzugt sind die Verbindungen der Formel Ib
The compounds of the formula Ib are also preferred

(I mit X = CH₂, R¹ und R² = Methyl, R⁶ = NO₂, R⁵ = H)
(I with X = CH ₂ , R ¹ and R ² = methyl, R ⁶ = NO ₂ , R ⁵ = H)

Bevorzugte Gruppen von Verbindungen sind weiterhin:Preferred groups of compounds are also:

Verbindungen Ic, die sich von den Verbindungen Ia dadurch unter scheiden, daß R⁴ Methoxy bedeutet.Compounds Ic, which differ from the compounds Ia in that R ^{4 is} methoxy.

Verbindungen Id, die sich von den entsprechenden Verbindungen Ia dadurch unterscheiden, daß R⁴ Brom bedeutet.Compounds Id, which differ from the corresponding compounds Ia in that R ^{4 is} bromine.

Verbindungen Ie, If und Ig, die sich von den entsprechenden Ver bindungen Ia, Ic und Id dadurch unterscheiden, daß R¹ Amino bedeu tet.Compounds Ie, If and Ig, which differ from the corresponding compounds Ia, Ic and Id in that R ^{1 is} amino.

Verbindungen Ih, Ii, Ij, Ik, Il und Im, die sich von den Verbin dungen Ia und Ic-Ig dadurch unterscheiden, daß X NH bedeutet.Connections Ih, Ii, Ij, Ik, Il and Im, which differ from the verbin differentiate Ia and Ic-Ig in that X means NH.

Die erfindungsgemaäßen Verbindungen der Formel I sind auf ver schiedene Weise erhältlich, insbesondere nach einem der folgenden Verfahren:The compounds of formula I according to the invention are based on ver available in various ways, especially one of the following Method:

Procedure A

Umsetzung eines Benzylharnstoffes mit Thioisocyanat auf an sich bekannte Weise lz. B. Tetrahedron Lett. 1990, 6763-6764) und an schließender Cyclisierung mit einer aktiven Kohlendioxidquelle wie Phosgen, Diphosgen, Triphosgen oder Carbodiimidazol.Implementation of a benzylurea with thioisocyanate itself known way lz. B. Tetrahedron Lett. 1990, 6763-6764) and an closing cyclization with an active carbon dioxide source such as phosgene, diphosgene, triphosgene or carbodiimidazole.

In der Regel cyclisiert man in einem inerten organischen Lösungs- oder Verdünnungsmittel, das aprotisch ist, beispielsweise in einem aliphatischen oder cyclischen Ether wie 1,2-Dimethoxyethan, Tetrahydrofuran und Dioxan, in einem Aromaten wie Benzol und Toluol oder in einem polaren Solvens wie Dimethylformamid und Dimethylsulfoxid. Auch Mischungen aus polarem Solvens und einem Kohlenwasserstoff wie n-Hexan sind geeignet. Je nach Ausgangs verbindung kann sich auch Wasser als Verdünnungsmittel eignen.
As a rule, cyclization is carried out in an inert organic solvent or diluent which is aprotic, for example in an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aromatic compound such as benzene and toluene or in a polar solvent such as dimethylformamide and dimethyl sulfoxide. Mixtures of polar solvent and a hydrocarbon such as n-hexane are also suitable. Depending on the starting compound, water can also be used as a diluent.

Wird bei der Cyclisierung HCl frei (z. B. beim Einsatz von Phos gen), empfiehlt sich der Einsatz einer Base.HCl is released during cyclization (e.g. when using Phos gen), the use of a base is recommended.

Als Basen kommen vorzugsweise Alkalimetallalkoholate, ins besondere die Natriumalkoholate, Alkalimetallhydroxide, ins besondere Natrium- und Kaliumhydroxid, Alkalimetallcarbonate, insbesondere Natrium- und Kaliumcarbonat, und Metallhydride, insbesondere Natriumhydrid, in Betracht. Bei der Verwendung von Natriumhydrid als Base hat es sich als vorteilhaft erwiesen, in einem aliphatischen oder cyclischen Äther, in Dimethylformamid oder in Dimethylsulfoxid zu arbeiten.Alkali metal alcoholates are preferably used as bases especially the sodium alcoholates, alkali metal hydroxides, ins special sodium and potassium hydroxide, alkali metal carbonates, especially sodium and potassium carbonate, and metal hydrides, especially sodium hydride. When using Sodium hydride as the base has been found to be advantageous in an aliphatic or cyclic ether, in dimethylformamide or to work in dimethyl sulfoxide.

Im allgemeinen ist die 0,5- bis zweifache molare Menge an Base, bezogen auf die Menge an III oder IV, für das Gelingen der Reaktion ausreichend.Generally the 0.5 to twice the molar amount of base, based on the amount of III or IV, for the success of the Reaction sufficient.

In der Regel liegt die Reaktionstemperatur zwischen (-78)°C und der Siedetemperatur des jeweiligen Reaktionsgemisches, insbesondere bei (-60) bis 60°C.The reaction temperature is usually between (-78) ° C and the boiling temperature of the respective reaction mixture, especially at (-60) to 60 ° C.

Üblicherweise wird das Verfahrensprodukt als Metallsalz erhalten, wobei das Metall dem Kation der verwendeten Base entspricht. Das Salz kann auf an sich bekannte Weise isoliert und gereinigt oder gewünschtenfalls mittels Säure in die freie Verbindung III über geführt werden. The process product is usually obtained as a metal salt, the metal corresponds to the cation of the base used. The Salt can be isolated and purified or in a manner known per se if desired by means of acid in the free compound III be performed.

Procedure B

Umsetzung eines 5-H Triazindionthions mit einem aktivierten Ben zylderivat. Dieses Verfahren ist besonders bevorzugt.
Implementation of a 5-H triazinedione thione with an activated benzyl derivative. This method is particularly preferred.

wobei L für eine Abgangsgruppe, insbesondere ein Halogenid steht.where L stands for a leaving group, in particular a halide.

Geeignete Basen sind beispielsweise Alkalimetallalkoholate wie Natriummethylat, Alkalimetallcarbonate wie Natrium- und Kalium carbonat oder Alkalimetallhydride wie Natrium- und Kaliumhydrid oder stickstoffhaltige Basen wie Triethylamin oder Pyridin.Suitable bases are, for example, alkali metal alcoholates such as Sodium methylate, alkali metal carbonates such as sodium and potassium carbonate or alkali metal hydrides such as sodium and potassium hydride or nitrogenous bases such as triethylamine or pyridine.

Es besteht auch die Möglichkeit, das 5-H-Triazindionthion mittels Base zunächst in das Alkalimetallsalz zu überführen und dieses dann anschließend mit IX umzusetzen.There is also the possibility of using the 5-H-triazinedione thione First convert base into the alkali metal salt and this then implement with IX.

Üblicherweise arbeitet man in einem inerten polaren Lösungs- oder Verdünnungsmittel, z. B. in Dimethylformamid, N-Methylpyrrolidon, in einem Sulfoxid wie Dimethylsulfoxid, in einem Carbonsäureester wie Ethylacetat, in einem Keton wie Aceton oder in einem Ether wie Diethylether und Tetrahydrofuran.Usually one works in an inert polar solution or Diluents, e.g. B. in dimethylformamide, N-methylpyrrolidone, in a sulfoxide such as dimethyl sulfoxide, in a carboxylic acid ester such as ethyl acetate, in a ketone such as acetone or in an ether such as diethyl ether and tetrahydrofuran.

In allgemeinen liegt die Reaktionstemperatur bei 0°C bis zur Siedetemperatur des Reaktionsgemisches.In general, the reaction temperature is from 0 ° C to Boiling temperature of the reaction mixture.

5-H-Triazindionthione können nach an sich bekannten Verfahren hergestellt werden (Angew. Chemie (1977), 789-796).5-H-triazinedione thiones can be prepared by methods known per se can be produced (Angew. Chemie (1977), 789-796).

Procedure C

Analog J. Chem. Soc. Perkin Trans. (1982), 1321
Analog J. Chem. Soc. Perkin Trans. (1982), 1321

Für die Bedingungen der Reaktion sei auf die genannte Literatur stelle verwiesen.For the conditions of the reaction, refer to the literature mentioned place referred.

Procedure D

Analog J. Chem. Soc. Perkin Trans. (1982), 1139
Analog J. Chem. Soc. Perkin Trans. (1982), 1139

Procedure E

Nach einem weiteren Verfahren werden die erfindungsgemäßen Ver bindungen I durch Umsetzung von Benzylisocyanaten mit Thioharn stoffen und anschließender Cyclisierung hergestellt.
According to a further process, the compounds I according to the invention are prepared by reacting benzyl isocyanates with thiourea and subsequent cyclization.

Gemäß einer besonders bevorzugten Ausführungsform des erfindungs gemäßen Verfahrens E wird das Isocyanat mit dem Thioharnstoff in Gegenwart einer aktivierten Kohlendioxidquelle umgesetzt. Bei spielhaft seien hier als bevorzugt Carbodiimidazol, Phosgen, Di phosgen und Triphosgen sowie Chlorameisensäureester genannt.According to a particularly preferred embodiment of the invention According to method E, the isocyanate with the thiourea in Implemented in the presence of an activated carbon dioxide source. At playable here are preferred as carbodiimidazole, phosgene, di phosgene and triphosgene and chloroformate called.

Die Verfahren (C) sowie die Verfahren (D) und (E) zur Herstel lung der Verbindungen der Formel) werden vorzugsweise in Gegen wart eines geeigneten Reaktionshilfsmittels durchgeführt.The processes (C) and the processes (D) and (E) for the manufacture tion of the compounds of formula) are preferably in counter a suitable reaction aid was carried out.

Als Reaktionshilfsmittel kommen im allgemeinen die üblichen an organischen oder organischen Basen oder Säureakzeptoren in Be tracht. Hierzu gehören vorzugsweise Alkalimetall- oder Erdalkali metall- -acetate, -amide, -carbonate, -hydrogencarbonate, hydride, -hydroxide oder -alkanolate, beispielsweise Natrium-, Kalium- oder Calciumacetat, Lithium-, Natrium-, Kalium- oder Calciumamid, Natrium-, Kalium- oder Calciumcarbonat, Natrium-, Kalium- oder Calciumhydrogencarbonat, Lithium-, Natrium-, Kalium- oder Calciumhydrid, Lithium-, Natrium-, Kalium- oder Calcium hydroxid, Natrium- oder Kaliummethanolat, -ethanolat, n- oder iso-propanolat, n-, iso-, sec- oder tert.-butanolat;The usual reaction aids generally arrive organic or organic bases or acid acceptors in Be dress. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, for example sodium, Potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, Potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or iso-propanolate, n-, iso-, sec- or tert-butanolate;

Das erfindungsgemäße Verfahren (C) sowie die Verfahren (A) und (B) zur Herstellung der Verbindung der Formel (I) werden vorzugs weise in Gegenwart eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen im allgemeinen die üblichen organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphati sche, alicyclische und aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, beispielsweise Pentan, Hexan, Heptan, Petro lether, Ligroin, Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Cyclohexan, Methylcyclohexan, Dichlormethan (Me thylenchlorid), Trichlormethan (Chloroform) oder Tetrachlorme than, Dialkylether wie Diethylether, Diisopropylether, Methyl tert.-butylether (MTBE), Ethyl-tert.-butylether, Methyltert.- pentylether (TAME), Ethyl-tert.-pentylether, Tetrahydrofuran (THF), 1,4-Dioxan, Ethylenglycol-dimethylether, Ethylenglycol diethylether, Diethylenglycol-dimethylether und -diethylether; Dialkylketone, wie Aceton, Butanon (Methylethylketon), Methyl isopropylketon und Methyl-isobutylketon; Nitrile wie Acetonitril, Propionitril, Butyronitril und Benzonitril; Amide wie N,N-Dime thylformamid (DMF), N,N-Dimethyl-acetamid, N-Methylformanilid, N-Methylpyrrolidon und Hexamethyl-phosphorsäuretriamid; Ester wie Essigsäure-methylester, -ethylester, -n-propylester, -isopropyle ster, -n-butylester, -isobutylester und -sec-butylester; Sulfo xide wie Dimethylsulfoxid;
Alkanole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-, iso-, sec.- und tert.-Butanol; Glycolether wie Ethylenglycol- monomethylether, -monoethylether, Diethylenglycol-monomethylether und -monoethylether; deren Gemische mit Wasser oder reines Wasser.Process (C) and processes (A) and (B) for the preparation of the compound of the formula (I) are preferably carried out in the presence of a diluent. The usual organic solvents are generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petro ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane ( Chloroform) or tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether, methyl tert-pentyl ether (TAME), ethyl tert-pentyl ether, tetrahydrofuran (THF), 1, 4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether and diethyl ether; Dialkyl ketones such as acetone, butanone (methyl ethyl ketone), methyl isopropyl ketone and methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile; Amides such as N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone and hexamethyl-phosphoric acid triamide; Esters such as methyl acetate, ethyl ester, n-propyl ester, isopropyl ester, n-butyl ester, isobutyl ester and sec-butyl ester; Sulfoxides such as dimethyl sulfoxide;
Alkanols such as methanol, ethanol, n-propanol, isopropanol, n-, iso-, sec- and tert-butanol; Glycol ethers such as ethylene glycol monomethyl ether, monoethyl ether, diethylene glycol monomethyl ether and monoethyl ether; their mixtures with water or pure water.

Die Reaktionstemperaturen können bei der Durchführung der Ver fahren (A) bis (E) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 0 bis 200°C, vor zugsweise bei 10 bis 150°C, insbesondere bei 20°C bis Siede temperatur des jeweiligen Reaktionsgemisches.The reaction temperatures can be carried out when carrying out the Ver drive (A) to (E) can be varied over a wide range. in the generally one works at temperatures from 0 to 200 ° C. preferably at 10 to 150 ° C, especially at 20 ° C to boiling temperature of the respective reaction mixture.

Zur Durchführung der Verfahren (A) bis (E) werden die Ausgangs stoffe im allgemeinen in angenähert äquimolaren Mengen einge setzt. Es ist jedoch auch möglich, jeweils eine der Komponenten in einem größeren Überschuß zu verwenden, etwa bis zur 2fachen molaren Menge der andere Komponente.To carry out processes (A) to (E), the starting substances generally in approximately equimolar amounts puts. However, it is also possible to use one of the components to be used in a larger excess, approximately up to 2 times molar amount of the other component.

Die Verfahren (A) bis (E) werden zweckmäßigerweise bei Atmosphä rendruck oder unter dem Eigendruck des jeweiligen Reaktionsgemi sches vorgenommen. Es ist jedoch auch möglich, die Verfahren un ter erhöhtem oder vermindertem Druck - im allgemeinen bei 0,1 bis 10 bar - durchzuführen.Processes (A) to (E) are expediently carried out at atmosphere pressure or under the autogenous pressure of the respective reaction mixture made. However, it is also possible to un ter increased or reduced pressure - generally at 0.1 to 10 bar - to be carried out.

Die Aufarbeitung der jeweiligen Reaktionsgemische erfolgt in der Regel nach an sich bekannten Methoden, beispielsweise durch Ver dünnen der Reaktionslösung mit Wasser und anschließender Iso lierung des Produktes mittels Filtration, Kristallisation oder Lösungsmittelextraktion, oder
durch Entfernen des Lösungsmittels, Verteilen des Rückstandes in einem Gemisch aus Wasser und einem geeigneten organischen Lösungsmittel und Aufarbeiten der organischen Phase auf das Produkt hin.The respective reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or
by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase onto the product.

Im allgemeinen sind die erfindungsgemäßen Verbindungen I nach einem der vorstehend genannten Syntheseverfahren herstellbar. Aus wirtschaftlichen oder verfahrenstechnischen Gründen kann es je doch zweckmäßiger sein, einige Verbindungen I aus ähnlichen 1-Benzyl-4-thiotriazinen - die sich jedoch insbesondere in der Bedeutung der Reste R⁵ oder R⁶ unterscheiden - herzustellen, und zwar auf an sich bekannte Weise, z. B. durch Esterhydrolyse, Veresterung, Amidierung, Acetalisierung, Acetalhydrolyse, Kon densationsreaktion, Wittig-Reaktion, Peterson-Olefinierung, Veretherung, Alkylierung, Oxidation oder Reduktion.In general, the compounds I according to the invention can be prepared by one of the synthesis processes mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar 1-benzyl-4-thiotriazines - which differ in particular in the meaning of the radicals R ⁵ or R ⁶ - in a manner known per se , e.g. B. by ester hydrolysis, esterification, amidation, acetalization, acetal hydrolysis, condensation reaction, Wittig reaction, Peterson olefination, etherification, alkylation, oxidation or reduction.

Die erfindungsgemäßen Verbindungen I können bei der Herstellung als Isomerengemische anfallen, die jedoch gewünschtenfalls nach den hierfür üblichen Methoden wie Kristallisation oder Chromato graphie, auch an einem optisch aktiven Adsorbat, in die reinen Isomeren getrennt werden können. Reine optisch aktive Isomere lassen sich vorteilhaft aus entsprechenden optisch aktiven Ausgangsprodukten herstellen.The compounds I according to the invention can be used in the preparation are obtained as mixtures of isomers, but if desired after the usual methods such as crystallization or chromato graph, also on an optically active adsorbate, into the pure Isomers can be separated. Pure optically active isomers can be advantageous from corresponding optically active Manufacture starting products.

Landwirtschaftlich brauchbare Salze der Verbindungen I können durch Reaktion mit einer Base des entsprechenden Kations, vor zugsweise einem Alkalimetallhydroxid oder -hydrid, oder durch Reaktion mit einer Säure des entsprechenden Anions, vorzugsweise der Chlorwasserstoffsäure, Bromwasserstoffsäure, Schwefelsäure, Phosphorsäure oder Salpetersäure, gebildet werden.Agricultural salts of the compounds I can by reaction with a base of the corresponding cation preferably an alkali metal hydroxide or hydride, or by Reaction with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, Phosphoric acid or nitric acid.

Salze von I, deren Metallion kein Alkalimetallion ist, können auch durch Umsalzen des entsprechenden Alkalimetall salzes in üblicher Weise hergestellt werden, ebenso Ammonium-, Phosphonium-, Sulfonium- und Sulfoxoniumsalze mittels Ammoniak, Phosphonium-, Sulfonium- oder Sulfoxoniumhydroxiden.Salts of I, the metal ion of which is not an alkali metal ion, can also by salting the corresponding alkali metal salt are prepared in the usual way, as well as ammonium, Phosphonium, sulfonium and sulfoxonium salts using ammonia, Phosphonium, sulfonium or sulfoxonium hydroxides.

Die Verbindungen I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die I enthaltenden herbiziden Mittel bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schad gräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of pure isomers - as herbicides. The herbicides containing I Agents fight plant growth on non-cultivated areas very well, especially with high application rates. In crops like wheat, rice, Corn, soybeans and cotton act against weeds and damage grasses without significantly damaging the crops. This The effect occurs especially at low application rates.

In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the respective application method, you can the compounds I or herbicidal compositions comprising them still in a number of crops for disposal unwanted plants can be used. Be considered for example the following cultures:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossyplum hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Tri folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays.Allium cepa, pineapple comosus, Arachis hypogaea, asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossyplum hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, sorghum bicolor (s. vulgare), Theobroma cacao, tri folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds I can also be used in cultures which through breeding including genetic engineering methods against the The effects of herbicides are tolerant.

Die Verbindungen I bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granu laten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewähr leisten.The compounds I or the herbicidal compositions comprising them can, for example, in the form of directly sprayable aqueous Solutions, powders, suspensions, including high-proof aqueous oily or other suspensions or dispersions, emulsions, Oil dispersions, pastes, dusts, spreading agents or granules laten by spraying, atomizing, dusting, scattering or Pouring can be applied. The application forms depend on the uses; in any case, they should be as possible guarantee the finest distribution of the active ingredients according to the invention Afford.

Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht: Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kerosin und Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromati sche Kohlenwasserstoffe, z. B. Paraffine, Tetrahydronaphthalin, alkylierte Naphthaline und deren Derivate, alkylierte Benzole und deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol und Cyclohexanol, Ketone wie Cyclohexanon, stark polare Lösungs- mittel, z. B. Amine wie N-Methylpyrrolidon und Wasser.The following are essentially considered as inert auxiliaries: Mineral oil fractions from medium to high boiling point such as Kerosene and diesel oil, as well as coal tar oils and vegetable oils or of animal origin, aliphatic, cyclic and aromatic cal hydrocarbons, e.g. B. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solution medium, e.g. B. amines such as N-methylpyrrolidone and water.

Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergier baren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die 1-Aryl-4-thiouracile I als solche oder in einem Öl oder Lösungs mittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgier mittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate herge stellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be made from emulsion concentrates, Suspensions, pastes, wettable powders or water dispersants granules can be prepared by adding water. For The production of emulsions, pastes or oil dispersions 1-aryl-4-thiouracile I as such or in an oil or solution medium solution, by means of wetting, adhesive, dispersing or emulsifying agents medium homogenized in water. But it can also come from active substance, wetting, adhesive, dispersing or emulsifying agent and possibly concentrates containing solvents or oil are provided, which are suitable for dilution with water.

Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z. B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether, Kondensati onsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether, Alkyl arylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylen oxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- oder Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids, e.g. B. lignin, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acids, alkyl and alkyl aryl sulfonates, alkyl and lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, condensates products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxy ethylenoctylphenolether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or Polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite waste liquors or methyl cellulose in Consideration.

Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for spreading and dusts can be mixed or joint grinding of the active substances with a solid Carrier are manufactured.

Granulate, z. B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe her gestellt werden. Feste Trägerstoffe sind Mineralerden wie Kiesel säuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Dünge mittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baum rinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. B. coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers be put. Solid carriers are mineral soils like pebbles acids, silica gels, silicates, talc, kaolin, limestone, lime, Chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and Magnesium sulfate, magnesium oxide, ground plastics, fertilizers agents such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or others solid carriers.

Die Konzentrationen der Wirkstoffe I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen etwa 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt. The concentrations of the active ingredients I in the ready-to-use Preparations can be varied in a wide range. Generally the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one Active ingredient. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum) used.

Die folgenden Formulierungsbeispiele verdeutlichen die Her stellung solcher Zubereitungen:
The following formulation examples illustrate the manufacture of such preparations:

A) 20 parts by weight of compound no. Ia.1 in one Dissolved mixture that alkylated from 80 parts by weight Benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanol amide, 5 parts by weight of calcium salt of dodecylbenzenesulfone acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By off pour and finely distribute the solution in 100000 weight divide water you get an aqueous dispersion that Contains 0.02% by weight of the active ingredient.
B) 20 parts by weight of compound no. Ia.1 are in one Dissolved mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the plant approximately 7 moles of ethylene oxide to 1 mole of isooctyl phenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By one pour and finely distribute the solution in 100000 weight divide water you get an aqueous dispersion that Contains 0.02% by weight of the active ingredient.
C) 20 parts by weight of active ingredient No. Ia.1 are in a Dissolved mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mole of castor oil consists. By pouring in and finely distributing the solution an aqueous solution is obtained in 100,000 parts by weight of water Dispersion containing 0.02% by weight of the active ingredient.
D) 20 parts by weight of active ingredient No. Ia.1 are with 3 parts by weight of the sodium salt of diisobutyl naphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel well mixed and ground in a hammer mill. By fine Distribute the mixture in 20,000 parts by weight of water contains a spray mixture containing 0.1% by weight of the active ingredient contains.
E) 3 parts by weight of active ingredient No. Ia.1 with 97 parts by weight of finely divided kaolin mixed. Man receives a dusting agent that contains 3% by weight contains the active substance.
F) 20 parts by weight of active ingredient No. Ia.1 with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight share sodium salt of a phenol-urea-formaldehyde Condensates and 68 parts by weight of a paraffinic Mineral oil mixed intimately. A stable oily is obtained Dispersion.
G) 1 part by weight of compound no. Ia.1 is in a Dissolved mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and There are 10 parts by weight of ethoxylated castor oil. Man receives a stable emulsion concentrate.
H) 1 part by weight of compound no. Ia.1 in one Mixture dissolved from 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (= non-ionic Emulsifier based on ethoxylated castor oil; BASF AG) exists. A stable emulsion concentrate is obtained.

Die Applikation der Wirkstoffe I bzw. der herbiziden Mittel kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by).The application of the active ingredients I or the herbicidal compositions can pre-emergence or post-emergence. Are the Active ingredients for certain crops less tolerable, so application techniques can be used in which the herbicidal agents are sprayed with the help of sprayers, that the leaves of sensitive crops if possible not to be taken while the active ingredients are on the leaves including growing unwanted plants or the uncovered Floor space (post-directed, lay-by).

Die Aufwandmengen an Wirkstoff I betragen je nach Bekämpfungs ziel, Jahreszeit, Zielpflanzen und Wachstumsstadium 0,001 bis 3,0, vorzugsweise 0,01 bis 1,0 kg/ha aktive Substanz (a. S.).The amount of active ingredient I depends on the control target, season, target plants and growth stage 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as described).

Zur Verbreiterung des Wirkungsspektrums und zur Erzielung syn ergistischer Effekte können die 1-Aryl-4-thiouracile I mit zahl reichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1,2,4-Thiadiazole, 1,3,4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, Aryloxy-/Heteroaryloxyälkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothiadi azinone, 2-(Hetaroyl/Aroyl)-1,3-cyclohexandione, Heteroaryl-Aryl- Ketone, Benzylisoxazolidinone, meta-CF₃-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclo hexan-1,3-dionderivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N-Phenyl-3, 4,5, 6-tetrahydrophthalimide, Oxadi azole, Oxirane, Phenole, Aryloxy- und Heteroaryloxyphenoxy- I propionsäureester, Phenylessigsäure und deren Derivate, 2-Phenyl propionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidyl ether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide und Uracile in Betracht.To broaden the spectrum of activity and to achieve syn ergistic effects, the 1-aryl-4-thiouracile I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together. For example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy- / heteroaryloxyalkanic acids and their derivatives, benzoic acid and their derivatives, benzothiadi azinones, 2- ( Hetaroyl / aroyl) -1,3-cyclohexanediones, heteroaryl-aryl ketones, benzylisoxazolidinones, meta-CF ₃ phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid , Dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4,5, 6-tetrahydrophthalimides, oxadi azoles , Phenols, aryloxy- and heteroaryloxyphenoxy- I propionic acid esters, phenylacetic acid and its derivatives, 2-phenyl propionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their Derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils into consideration.

Außerdem kann es von Nutzen sein, die Verbindungen I allein oder in Kombination mit anderen Herbiziden auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch nicht-phytotoxische Öle und Ölkonzentrate zugesetzt werden.Compounds I alone may also be useful or in combination with other herbicides also with others Mixed crop protection products to apply together, for example with pest control agents or phytopathogenic fungi or bacteria. It is also of interest the miscibility with mineral salt solutions, which are used to eliminate Nutritional and trace element deficiencies are used. It can non-phytotoxic oils and oil concentrates can also be added.

Examples 5- (2 ', 3'-dichloro-4'-methoxy) phenyl-1,3-dimethyltriazinedione thione

Zu einer Mischung aus 1 g (0,0057 mol< 1,3-Dimethyltriazindiont hion und 0,85 g (0,0062 mol) Kaliumcarbonat in 50 ml DMF wurden bei Raumtemperatur 1,62 g (0,006 mol) 2,3-Dichlor-4-methoxyben zylbromid gegeben. Nach 17 h wurden 50 ml Eiswasser zugegeben. Der ausgefallene Niederschlag wurde abfiltriert und mit Wasser gewaschen.
Ausbeute: 1,5 g (75%); Fp. 195-197°CTo a mixture of 1 g (0.0057 mol <1,3-dimethyltriazinedione hione and 0.85 g (0.0062 mol) potassium carbonate in 50 ml DMF was added 1.62 g (0.006 mol) 2,3-dichloro at room temperature -4-methoxybenzyl bromide was added and after 17 h 50 ml of ice water were added, the precipitate was filtered off and washed with water.
Yield: 1.5 g (75%); Mp 195-197 ° C

5- (2 ', 3'-dichloro-4'-hydroxy) phenyl-1,3-dimethyltriazinedione thione

1,1 g(0,003 mol) 5-(2',3'-Dichlor-4'-Hydroxy)phenyl-1,3-dimethyl triazindionthion in eo ml Dichlormethan wurden bei Raumtemperatur mit 6 ml (0,006 mol) einer 1-molaren BBr3-Lösung in Dichlormethan versetzt. Nach 17 h Rühren bei Raumtemperatur und zwei Stunden bei 40°C wurde diese Mischung in 200 ml Eiswasser gegeben. Der ausge fallene Niederschlag wurde abfiltriert.
Ausbeute: 0,55 g (52%); Fp. 255-256°C 1.1 g (0.003 mol) of 5- (2 ', 3'-dichloro-4'-hydroxy) phenyl-1,3-dimethyl triazinedione thione in eo ml of dichloromethane were treated with 6 ml (0.006 mol) of a 1 molar at room temperature BBr3 solution in dichloromethane. After stirring at room temperature for 17 hours and at 40 ° C. for two hours, this mixture was added to 200 ml of ice water. The precipitate was filtered off.
Yield: 0.55 g (52%); Mp 255-256 ° C

Aus der organischen Phase konnten noch 0,22 g des Ausgangsmate rials isoliert werden.0.22 g of the starting material could still be obtained from the organic phase rials are isolated.

5- (2 ', 3'-dichloro-4' - (2 "-ethoxycarbonyl-2" -ethoxyiminoethoxy) phenyl-1,3-dimethyltriazinedione thione

Zu einer Mischung aus 0,43 g (0,0012 mol) 5-(2',3'-Dichlor-4'-Hy droxy)phenyl-1,3-dimethyltriazindionthion und 0,34 g (0,0024 mol) Kaliumcarbonat in 30 ml Dimethylformamid (DMF) wurden bei Raum temperatur 0,36 g (0, 0015 mol) 2-Ethoxycarbonyl-2-Ethoxyiminoe thylbromid gelöst in 5 ml DMF getropft. Nach 17 h Rühren wurden 50 ml Eiswasser zugegeben. Der ausgefallene Niederschlag wurde abfiltriert und mit Wasser und Petrolether gewaschen.
Ausbeute: 0,55 g (88%); Fp. 114-116°C.To a mixture of 0.43 g (0.0012 mol) of 5- (2 ', 3'-dichloro-4'-hydroxy) phenyl-1,3-dimethyltriazinedione thione and 0.34 g (0.0024 mol) of potassium carbonate in 30 ml of dimethylformamide (DMF), 0.36 g (0.0015 mol) of 2-ethoxycarbonyl-2-ethoxyiminoethyl bromide dissolved in 5 ml of DMF were added dropwise at room temperature. After stirring for 17 h, 50 ml of ice water were added. The precipitate was filtered off and washed with water and petroleum ether.
Yield: 0.55 g (88%); Mp 114-116 ° C.

In analoger Weise wurden die in den nachstehenden Tabellen aufge führten Verbindungen hergestellt (die Bezeichnungen Ia und Ib be ziehen sich auf die entsprechenden Verbindungen in Tabelle 1.
The compounds listed in the tables below were prepared in an analogous manner (the designations Ia and Ib refer to the corresponding compounds in Table 1.

Claims

1. New 5- (benz (o) yl / anilino) triazinedione thiones of the formula I
where the variables have the following meanings:
X -CH ₂ , -C (= O) -or -NH-;
R ¹ , R ^{2 are} methyl or amino;
R ^{3 is} hydrogen, cyano, thiocyanato, halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio;
R ^{4 is} hydrogen, cyano, halogen, thiocyanato, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkoxy, C ₂ -C ₆ alkenoxy , C ₂ -C ₆ alkynoxy, C ₁ -C ₆ alkoxycarbonyl, C ₂ -C ₆ alkenoxycarbonyl, C ₂ -C ₆ alkynoxycarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ hydroxyalkylcarbonyl , C ₁ -C ₄ alkylsulfonylamino or amino, where the last 7 radicals can carry one of the following substituents: C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, amino or C ₁ -C ₄ alkylsulfonylamino;
R ⁵ at position α or β is hydrogen, cyano, nitro, halogen or C ₁ -C ₄ alkoxy;
R ⁶ at position α, R5 then at position β,

1. hydrogen, cyano, nitro, halogen, amino,
2. C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkylthio, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkylthio; C ₂ -C ₆ alkenyloxy, C ₅ -C ₇ cyclo alkenyloxy, C ₂ -C ₆ alkenylthio, C ₂ -C ₆ alkynyloxy, C ₂ -C ₆ alkynylthio, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₁ -C ₆ alkyl) carbonylthio, (C ₁ -C ₆ alkoxy) carboxyloxy, (C ₂ -C ₆ alkenyl) carbonyloxy, (C ₂ -C ₆ alkenyl) carbonyl thio, (C ₂ -C ₆ -alkynyl) carbonyloxy, (C ₂ -C ₆ -alkynyl) -carbonylthio, C ₁ -C ₆ -alkylsulfonyl or C ₁ -C ₆ -alkyl sulfonyloxy, each of the latter 18 radicals being able to carry one to four substituents if desired , each selected from the group consisting of
- - Halogen, nitro, cyano, hydroxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₅ cycloalkyloxy, C ₃ -C ₆ alkenyl oxy, C ₃ -C ₆ alkynyloxy , C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylidene aminoxy,
- - The phenyl, phenoxy or phenylsulfonyl group, which may be unsubstituted or bear one to three sub-substituents, each selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl , C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl,
- - A 3- to 7-membered heterocyclyl or heterocyclyloxy group, which can carry one to three substituents, each selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy , C ₁ -C ₆ haloalkyl and (C ₁ -C ₆ alkyl) carbonyl,
- - an oxygen atom bound via a double bond,
- - A group -CO-R ⁷ -CO-OR ⁷ , -CO-SR ⁷ , -CO-N (R ⁷ ) R ⁸ , -OCO-R ⁷ , -OCO-OR ⁷ , -OCO-SR ⁷ , OCO -N (R ⁷ ) R ⁸ or -N (R ⁷ ) R ⁸ ,
- - A group = N-OR ⁹ , -C (R ¹⁰ ) = N-OR ⁹ or Si (R ¹¹ , R ¹² , R ¹³ ), where R ¹¹ , R ¹² and R ¹³ independently of one another for C ₁ -C ₆ Alkyl or C ₂ -C ₆ alkenyl;
3. -CY-R ¹⁴ , -C (R ¹⁴ ) (Z ¹ R ¹⁵ ) (Z ² R ¹⁶ ), where Z ¹ and Z ² each represent oxygen or sulfur, -C (R ¹⁴ ) = C (R ¹⁷ ) -CN, -C (R ¹⁴ ) = C (R ¹⁷ ) -CO-R ¹⁸ , -CH (R ¹⁴ ) -CH (R ¹⁷ ) -CO-R ¹⁸ , -C (R ¹⁴ ) = C ( R ¹⁷ ) -CH ₂ -CO-R ¹⁸ , -C (R ¹⁴ ) = C (R ¹⁷ ) -C (R ¹⁹ ) = C (R ²⁰ ) -CO-R ¹⁸ , -C (R ¹⁴ ) = C (R ¹⁷ ) -CH ₂ -CH (R ²¹ ) -CO-R ¹⁸ , -CO-OR ²² , -C ∼ C-CO-NH-OR ⁹ , -C ∼ C-CO-N (R ²² ) - OR ⁹ , -C ∼ C-CS-NH-OR ⁹ , -C ∼ C-CS-N (R ²² ) -OR ⁹ , -C ∼ CC (R ¹⁰ ) = N-OR ⁹ , -C (R ¹⁴ ) = C (R ¹⁷ ) -CO-NH-OR ⁹ , -C (R ¹⁴ ) = C (R ¹⁷ ) -CO-N (R ²² ) -OR ⁹ , -C (R ¹⁴ ) = C (R ¹⁷ ) -CS-NH-OR ⁹ , -C (R ¹⁴ ) = C (R ¹⁷ ) -CS-N (R ²² ) -OR ⁹ , -C (R ¹⁴ ) = C (R ¹⁷ ) -C (R ¹⁰ ) = N-OR ⁹ , -N (R ²⁴ ) R ²⁵ ,
where Alk is C ₁ -C ₃ alkylene which can carry a C ₁ -C ₆ alkyl substituent;
4. -CO-N (R ²² ) -OR ⁹ , -C (R ¹⁰ ) = N-OR ⁹ , -C (Z ¹ R ¹⁵ ) (Z ² R ¹⁶ ) OR ²³ , -C (Z ¹ R ¹⁵ ) (Z ² R ¹⁶ ) SR ²³ , -C (Z ¹ R ¹⁵ ) (Z ² R ¹⁶ ) NR ²⁴ R ²⁵ ,
-COO-R ²³ , -COS-R ²³ , -CON (R ²⁴ ) R ²⁵ , C ₁ -C ₆ alkylthio- (C ₁ -C6 alkyl) carbonyl or (C ₁ -C ₆ alkyl) iminooxycarbonyl,

R ^{7 represents} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) carbonyl-C ₁ -C ₆ -alkyl, (C ₃ -C ₆ -alkenyloxy) carbonyl-C ₁ -C ₆ -alkyl, phenyl or phenyl-C ₁ -C ₆ alkyl, where the phenyl group and the phenyl ring of the phenyl alkyl group may be unsubstituted or may carry one to three radicals, each selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ -Halogenalkyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkyl) carbonyl
and
R ^{8 is} hydrogen, hydroxy, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, (C ₁ -C ₆ alkoxy) carbonyl-C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkenyloxy,
stand, or R ⁷ and R ⁸ together with the common nitrogen form a 3- to 7-membered heterocyclyl group, which in turn can carry one to three substituents, each selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₆ Alkyl, C ₁ -C ₆ haloalkyl C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkyl) carbonyl;
R ^{9 is} hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, hydroxy-C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylthio-C ₁ -C ₆ alkyl, cyano-C ₁ -C ₆ alkyl, (C ₁ -C ₆ -alkyl) carbonyl-C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) carbonyl-C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) carbonyl-C ₂ -C _6- alkenyl, (C ₁ -C ₆ -alkyl) carbonyloxy-C ₁ -C ₆ -alkyl or phenyl-C ₁ -C ₆ -alkyl, where the phenyl ring can optionally carry one to three substituents, each selected from the group consisting of from cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl;
R ¹⁰

- hydrogen, halogen,
C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₁ -C ₆ alkyl thio, C ₁ -C ₆ haloalkylthio, (C ₁ -C ₆ alkyl) carbonyl oxy, (C ₁ -C ₆ haloalkyl) carbonyloxy, C ₁ -C ₆ alkyl sulfonyloxy or C ₁ -C ₆ haloalkylsulfonyloxy, where the the latter 11 radicals can carry one of the following substituents: hydroxy, cyano, hydroxy carbonyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ -Alkoxy) carbonyl, (C ₁ -C ₆ -alkylamino) carbonyl, di- (C ₁ -C ₆ -alkyl) amino carbonyl, (C ₁ -C ₆ -alkyl) carbonyloxy,
a 3- to 7-membered azaheterocycle which is bonded to the nitrogen atom via a carbonyl bridge and which, in addition to carbon ring members, can also contain an oxygen or sulfur atom as the ring member,
- (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ haloalkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkoxy) carbonyloxy, (C ₁ -C _6- alkyl) carbonylthio, (C ₁ -C ₆ -haloalkyl) carbonylthio, (C ₁ -C ₆ -alkoxy) carbonylthio, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenylthio, C ₃ -C ₆ - Alkynyl, C ₃ -C ₆ -alkynyloxy, C ₃ -C ₆ -alkynylthio, (C ₂ -C ₆ -alkynyl) carbonyloxy, C ₃ -C ₆ -alkynylsulfonyloxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C _6- cycloalkyloxy, C ₃ -C ₆ -cycloalkylthio, (C ₃ -C ₆ -cycloalkyl) carbonyl oxy, C ₃ -C ₆ -cycloalkylsulfonyloxy,
- Phenyl, phenoxy, phenylthio, benzoyloxy, phenyl sulfonyloxy, phenyl-C ₁ -C ₆ -alkyl, phenyl-C ₁ -C ₆ -alkoxy, phenyl-C ₁ -C ₆ -alkylthio, phenyl- (C ₁ -C ₆ -alkyl) carbonyloxy or phenyl- (C ₁ -C ₆ -alkyl) sulfonyloxy, where the phenyl rings of the latter 10 radicals may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl;

R ^{14 is} hydrogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl or (C ₁ -C ₆ -alkoxy) carbonyl;
R ¹⁵ , R ¹⁶ independently of one another are C ₁ -C ₆ alkyl, C ₁ -C ₆ halo alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy- C ₁ -C ₆ alkyl or
R ¹⁵ and R ¹⁶ together form a saturated or unsaturated, two- to four-membered carbon chain which can carry an oxo substituent, it being possible for one link in this chain to be replaced by an oxygen, sulfur or nitrogen atom which is not adjacent to variables 21 and 22, and wherein the carbon chain can also carry one to three radicals, each selected from the group consisting of cyano, nitro, amino, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ - Alkoxy, Ca-C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, C ₁ -C ₆ -haloalkyl, cyano-C ₁ -C ₆ -alkyl, hydroxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -Alkoxy-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyloxy-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkynyloxy-C ₁ -C ₆ -alkyl, C ₃ -C ₆ - Cycloalkyl, C ₃ -C ₆ cycloalkoxy, carboxy, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkyl) carbonyl oxy-C ₁ -C ₆ alkyl and phenyl, which in turn is unsubstituted or can carry one to three substituents, each selected from the group consisting of cyano, nitro , Amino, halo, C ₁ -C ₆ alkyl, C ₁ -C ₆ -halogen alkyl, C ₁ -C ₆ -alkoxy and (C ₁ -C ₆ alkoxy) carbonyl, and where one or two members of the carbon chain and Can be part of a three- to seven-membered ring, which can contain one or two heteroatoms as ring members, selected from oxygen, sulfur, nitrogen and nitrogen substituted by C ₁ -C ₆ alkyl, and, if desired, in turn one or two of the following substituents can carry: cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ alkoxy, cyano-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and (C ₁ -C ₆ alkoxy) carbonyl;
R ^{17 is} hydrogen, cyano, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkyl) carbonyl or (C ₁ -C ₆ Alkoxy) carbonyl;
R ^{18 is} hydrogen, OR ²³ , SR ²³ , C ₁ -C ₆ alkyl, which can also carry one or two C ₁ -C ₆ alkoxy substituents, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkylthio-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyliminooxy, -N (R ²⁴ ) R ²⁵ or phenyl, which can be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ halo alkyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl, where R ^{23 represents} one of the meanings of R ²² ,
R ^{19 is} hydrogen, cyano, halogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, -N (R ²⁶ ) R ²⁷ , where R ²⁶ and R ²⁷ stand for one of the meanings of R ²⁴ and R ²⁵ , or
Phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ halo alkyl, C ₃ -C ₆ alkenyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl;
R ^{20 is} hydrogen, cyano, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₅ alkoxy, C ₁ -C ₆ haloalkyl, (C ₁ -C ₆ alkyl) carbonyl or (C ₁ -C ₆ - Alkoxy) carbonyl;
R ^{21 is} hydrogen, cyano, C ₁ -C ₆ alkyl or (C ₁ -C ₆ alkoxy) carbonyl;
R ^{22 is} hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, where the latter 4 groups can each carry one or two of the following radicals : Cyano, halogen, hydroxy, hydroxycarbonyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₃ -C ₆ alkenyloxy) carbonyl or a 3- to 7-membered azaheterocycle bonded to the nitrogen atom via a carbonyl bridge, which ring members may contain an oxygen or sulfur atom as a ring member in addition to carbon members ;
or (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ haloalkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylaminocarbonyl, di- (C ₁ -C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkyloximino C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl,
or (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ haloalkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylaminocarbonyl, di- (C ₁ -C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkyloximino C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl,
Phenyl or phenyl-C ₁ -C ₆ -alkyl, where the phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ -alkyl, C ₁ - C ₆ haloalkyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl;
R ²⁴ , R ²⁵ independently of one another are hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbony1, (C ₁ -C ₆ alkoxy) carbonyl C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxy) carbonyl-C ₂ -C ₆ alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals,
or for C ₁ -C ₆ -alkylsulfonyl, (C ₁ -C ₆ -alkoxy) carbonyl-C ₁ -C ₆ -alkylsulfonyl, phenyl, phenylsulfonyl, benzyl or benzylsulfonyl where the four phenyl rings are unsubstituted or in turn one to three substituents can wear, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl, C ₁ -C ₆ alkoxy and ( C ₁ -C ₆ alkoxy) carbonyl, or or
R ²⁴ and R ²⁵ together with the common nitrogen atom form a saturated or unsaturated 4- to 7-membered azaheterocycle which, if desired, can contain one of the following members in addition to carbon ring members: -O-, -S-, -N =, -NH- or -N (C ₁ -C ₆ alkyl) -;
Y is oxygen, sulfur or -N (R ²⁸ ) -, wherein
R ²⁸ for hydrogen, hydroxy, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ haloalkyl, C ₁ - C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₃ -C ₆ cycloalkyloxy, C ₅ -C ₇ -Cycloalkenyl oxy, C ₁ -C ₆ -haloalkoxy, C ₃ -C ₆ -haloalkenyloxy, hydroxy-C ₁ -C ₆ -alkoxy, cyano-C ₁ -C ₆ -alkoxy, C ₃ -C ₆ -cyclo-alkyl- C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy-C ₃ -C ₆ alkenyloxy, (C ₁ -C ₆ alkyl) carbonyloxy , (C ₁ -C ₆ haloalkyl) carbonyloxy, (C ₁ -C ₆ alkyl) carbamoyl oxy, (C ₁ -C ₆ haloalkyl) carbamoyloxy, (C ₁ -C ₆ alkyl) carbonyl-C ₁ -C _6- alkyl, (C ₁ -C ₆ alkyl) carbonyl-C ₁ -C ₆ alkoxy, (C ₁ -C ₆ alkoxy) carbonyl -C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxy ) carbonyl-C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio-C ₁ -C ₆ -alkoxy, di- (C ₁ -C ₆ -alkyl) amino-C ₁ -C ₆ -alkoxy,
Phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ halo alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl,
Phenyl-C ₁ -C ₆ -alkoxy, phenyl-C ₃ -C ₆ -alkenyloxy or phenyl - C ₃ -C ₆ -alkynyloxy, where in each case one or two methylene groups of the carbon chains by -O-, -S- or -N (C ₁ -C ₆ alkyl) - can be replaced and each phenyl ring can be unsubstituted or in turn carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl,
Heterocyclyl, heterocyclyl-C ₁ -C ₆ -alkoxy, heterocyclyl-C ₃ -C ₆ -alkenyloxy or heterocyclyl-C ₃ -C ₆ -alkynyloxy, where in each case one or two methylene groups of the carbon chains by -O-, -S- or -N (C ₁ -C ₆ alkyl) - can be replaced and each heterocycle is three to seven-membered and in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl, or -N (R ²⁹ ) R ³⁰ ,
where R ²⁹ and R ³⁰ each represent hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl- C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxy) carbonyl-C ₂ -C ₆ alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or for phenyl, which may be unsubstituted or in turn carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl, C ₁ -C ₆ alkoxy and (C ₁ -C ₆ alkoxy) carbonyl,
or R ²⁹ and R ³⁰ together with the common nitrogen atom form a saturated or unsaturated 4- to 7-membered heterocycle which, if desired, may contain one of the following members in addition to carbon ring members: -O-, -S-, -N =, - NH- or -N (C ₁ -C ₆ alkyl) -;
and the agriculturally useful salts and enol ethers of the compounds I.

2. 5- (Benz (o) yliAnilino) triazinedione thiones of the formula I according to claim 1, where X is -CH ₂ - or -NH-.

3. 5- (Benz (o) yl / anilino) triazinedione thiones of the formula I according to claim 1, wherein R ^{3 is} hydrogen or halogen.

4. 5- (Benz (o) yl / anilino) triazinedione thiones of the formula I according to claim 1, where R ^{4 is} halogen, C ₁ -C ₄ alkoxy, C ₂ -C ₆ alkenoxy, C ₂ -C ₆ - Alkinoxy, C ₁ -C ₄ alkoxycarbonyl, C ₂ -C ₆ alkenoxycarbonyl, or C ₂ -C ₆ alkynoxycarbonyl.

5. 5- (Benz (o) yl / anilino) triazinedione thiones of the formula I according to claim 1, where R5 is hydrogen, halogen or C ₁ -C ₄ alkoxy.

6. Use of the 5- (benz (o) yl / anilino) triazinedione thiones of formula I and their agriculturally useful salts and enol ethers as claimed in claim 1 as herbicides.

7. Herbicidal composition containing a herbicidally effective amount at least one 5- (benz (o) yl / anilino) triazinedione thione Formula I or an agricultural salt or enol ether of I, according to claim 1, and at least an inert liquid and / or solid carrier and if desired, at least one surfactant.

8. Process for the preparation of herbicidally active agents, characterized in that a herbicidally effective amount at least one 5- (benz (o) yl / anilino) triazinedione thione Formula I or an agricultural salt or enol ether of I, according to claim 1, and at least an inert liquid and / or solid carrier and if desired, at least one surfactant mixes.

9. a method for controlling undesirable plant growth, characterized in that a herbicidally effective amount at least one 5- (benz (o) yl / anilino) triazinedione thione Formula I or an agricultural salt or enol ether of I, according to claim 1, on plants whose Habitat or on seeds.

10. Process for the preparation of compounds I
wherein the variables have the meaning given in claim 1, by reacting a 5-H-triazinedione thione with an activated benzyl derivative in the presence of a base
where L stands for a leaving group.