SK497A3 - 1,2,4,6-thiatriazines, preparation method thereof, herbicidal agents containing them and their use - Google Patents

Abstract

Compounds of formula (I), in which R1 is a substituent bonded via a carbon atom, R4 is a substituent, R2 and R3 are hydrogen or substituents and X is O, S, SO or SO2, are suitable as herbicides.

Description

Technical field

The invention relates to novel active thiatriazine derivatives, to processes for their preparation, to compositions containing them, to their use for weed control, in particular in crop plants or for inhibiting growth.

BACKGROUND OF THE INVENTION

Thiatriazine compounds are described, for example, in Chem. Ber. 121, 383-386 (1988), Z. Naturforsch. 43, 763-768 (1988), Chem. Ber. 126, 2601-2607 (1993), J. Am. Chem Soc. 1989, 111, 1180 - 1185, DD 113 006 and in his PhD thesis by W. Júrgler, Philipps-University Marburg / Lahn, 1988 (4λ ⁴ - and 1 λ ^e -2,4,6-Thiatriazine aus Sulfodiimiden).

2H-1,2,4,6-thiatriazine-1,1-dioxides are disclosed as herbicides in EP-A-0 075 117.

We have now found a new and simple synthesis method for the preparation of novel thiatriazine derivatives which are substituted with a number of substituents. The advantages of this method of synthesis are not only the easy availability of thiatriazine derivatives which are substituted by a series of substituents, but also the low number of synthetic steps (transformations). In addition, herbicidal and plant growth inhibitory properties of thiatriazine derivatives were first discovered.

SUMMARY OF THE INVENTION

The invention thus provides compounds of formula I

R

N

N \\ // to nr ² r ³ (I)

X-R in which

R ¹ represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkylalkyl group having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 17 carbon atoms in the alkyl moiety, alkylcycloalkyl having 1 to 17 carbon atoms C 3 -C 8 alkyl, C 2 -C 17 alkenyl, C 3 -C 8 cycloalkyl and C 2 -C 17 alkenyl, C 2 -C 17 alkenylcycloalkyl C3-C8 alkenyl, C3-C8 alkynyl, cycloalkylalkynyl and C2-C7 alkynyl, C2-C7 alkynylcycloalkyl and C3-C8 alkynyl carbon in the cycloalkyl moiety, a cycloalkenyl group of 5 to 8 atoms C 5 -C 8 cycloalkenylalkyl having 1 to 17 carbon atoms in the alkyl moiety, C 1 -C 17 alkylcycloalkenyl having 5 to 8 carbon atoms in the cycloalkenyl moiety, C 5 -C 8 cycloalkenylalkenyl carbon atoms in the cycloalkenyl and 2 to 17 carbon atoms in the alkenyl moiety, alkenylcycloalkenyl having 2 to 17 carbon atoms in the alkenyl moiety and 5 to 8 carbon atoms in the cyclopine of the 2 to 17 alkenyl moiety, a cycloalkenylalkinyl group of 5 up to 8 carbon atoms in the cycloalkenyl moiety and 2 to 17 carbon atoms in the alkynyl moiety, alkynylcycloalkenyl of 2 to 17 carbon atoms in the alkynyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, a cycloalkylcycloalkyl group of 3 to 8 carbon atoms in each cycloalkyl moiety C 5 -C 8 cycloalkenylcycloalkenyl and in each cycloalkenyl moiety, cycloalkylcycloalkenyl of 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylcycloalkyl of 5 to 8 carbon atoms in the cycloalkenyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety (C 2 -C 17) alkynyl and (C 2 -C 17) alkenyl or (C 2 -C 17) alkenyl (C 2 -C 17) alkynyl, which groups may be halogen substituted, cyano , nitro, oxo, -OR ^S , -S (O) R ^s , n

-COOR ⁷ , -CONR ® R ⁹ , -NR ¹⁰ R ¹³ , = NR ¹² , = N-NR ¹³ R ¹⁴ , phenyl, biphenyl, naphthyl or heterocyclyl, wherein the phenyl, naphthyl and heterocyclyl substituents may be: be substituted by halogen, cyano, nitro, ^-OR, -NR ¹ 'R ¹¹ or -CONR ⁸ R®, and

R ¹ represents a heterocyclyl group, the heterocycle being attached to the thiatriazine ring via one of its carbon atoms and wherein the heterocycle may be substituted by halogen, cyano, nitro, oxo, -OR ^S , -S (O) R ⁶ , -COOR ⁷ , n

CONR ^a R ^9, -NR ^X1 R ^{1 O,} = NR ^12, = N-NR ¹³ R ^14, an alkyl group having 1 to 17 carbon atoms, alkenyl group having 2 to 17 carbon atoms, alkynyl group having 2 to 17 carbon atoms C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, phenyl, biphenyl, naphthyl, C 1 -C 17 alkyl substituted with halogen, cyano, nitro, -OR ³ , -CONR ^and R ⁹ or -NR ^XO R ^XX , a C 2 -C 17 alkenyl substituted with halogen, cyano, nitro, -OR ³ , -CONR ^S R ® or -NR ^XO R ^XX , alkynyl (C 2 -C 17) -substituted by halogen, cyano, nitro, -OR ³ , -CONR ® R (R) or -NR ^XO R ( ^XX) , C 3 -C 8 -cycloalkyl substituted by halogen, cyano, nitro, -OR ³ , -CONR ^and R ⁹ or -NR ^XO R ^XX , a C 5 -C 8 cycloalkenyl group substituted with halogen, cyano, nitro, -OR ³ , -CONR ⁸ R ⁹ or -NR ^XO R ^XX , phenyl which is substituted by halogen, cyano, nitro, -OR ³ , -CONR ^and R ⁹ or -NR ^XO R ^XX , a biphenyl group substituted by halogen, cyano, nitro, -OR ^S , -CONR ^and R ^9, or -NR ^XO R ^XX or a naphthyl group substituted with halogen, cyano, nitro, -OR ³ , -CONR ^and R ⁹ , or -NR ^XO R ^XX or

R ^x represents a phenyl group, a biphenyl group, a naphthyl group, an alkylphenyl group having 1 to 10 carbon atoms in the alkyl moiety, an alkylbiphenyl group having 1 to 10 carbon atoms in the alkyl moiety, an alkylnaphthyl group having from 1 to 10 C 2 to C 10 alkenyl, C 2 to C 10 alkenyl, C 2 to C 10 alkenyl, naphthyl, C 2 -C 10 alkynyl, C 2 -C 10 alkynyl C10 -alkynyl or alkinylnaftylovú of 2 to 10 carbon atoms in the alkynyl part, which groups may be substituted by halogen, cyano, nitro, -0R ^p, s (0) R®, -COOR ^-7 - CONR ^S R ⁹ or -NR ^XO R ^{1 L,} wherein n

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 5 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 2 -C 7 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino carbon atoms, -N = CH ₂ , -N = CH-alkyl of 1 to 4 carbon atoms in the alkyl moiety, -N = C (alkyl) ₂ of 1 to 4 carbon atoms in each alkyl moiety, trialkylsilyl C3 -C6 cycloalkyl, C3 -C7 cycloalkyl, C2 -C7 alkenyl or C3 -C7 alkynyl, n has the value 0, 1, or 2

R 8 represents a hydrogen atom or a cyano group when n is 0, or

R @ 5 is C1 -C5 alkyl, C1 -C5 haloalkyl, C1 -C5 hydroxyalkyl, phenyl, naphthyl, C1 -C4 alkylphenyl, alkylnaphthyl (C 1 -C 4) -alkyl, halo-6-phenylphenyl, halo-phthyl, heterocyclyl, halo-heterocyclyl or (C 3 -C 7) cycloalkyl,

R ^v is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 6 nitroalkyl, C 1 -C 6 cyanoalkyl, phenyl, naphthyl, halophenyl , halo-phenyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkylcarbonyl, heterocyclyl, halo-heterocyclyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halo-cycloalkyl-N, CH _2, N = CH-C 1 -C 4 alkyl, a group -N = C (alkyl) ₂ having 1 to 4 carbon atoms, alkylamino or dialkylamino having 2 to 6 carbon atoms; R R @ 7 and R @ ⁹ are each independently hydrogen, phenyl, naphthyl, halophenyl, halophthyl or alkyl; C 1 -C 8 haloalkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, phenoxy, naphthoxy, halophenoxy, halo-phenoxy, C 2 -C 7 cyanoalkyl, C 3 -C 7 alkenyl , (C 3 -C 7) alkynyl, (C 2 -C 8) alkoxyalkyl, -N = CH ₂ , -N = CH-C 1 -C 4 -alkyl,-N = C (alkyl) ₍ C 1 -C 4) in each alkyl moiety, (C 1 -C 6) alkylamino or (C 2 -C 6) dialkylamino, or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which: may be halogenated; R ¹⁰ and R ¹¹ independently of one another are hydrogen, phenyl, naphthyl, halophenyl, halogénnaftylovú, alkyl of 1 to 8 carbon C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, phenoxy, naphthoxy, halo-phenoxy, halo-phenoxy, (C 2 -C 7) cyanoalkyl, (C 3 -C 7) alkenyl; up to 7 carbon atoms, 2 to 8 carbon alkoxyalkyl, -N = CH ₂ , -N = CH-alkyl of 1 to 4 carbon atoms in the alkyl moiety,-N = C (alkyl) _{2 of} 1 to 7 carbon atoms; C 4 -C 6 alkyl, C 1 -C 6 alkylamino or C 2 -C 6 dialkylamino, formyl, C 2 -C 8 alkylcarbonyl, phenylcarbonyl or naphthylcarbonyl, the phenyl or naphthyl radical in these groups it may be substituted by C1-C4alkyl, halogen, C1-C4alkoxy, hydroxy, cyano ω, nitro or C 2 -C 6 alkoxycarbonyl, or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated,

R 1a is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, phenyl, halogenphenyl, cyanophenyl, nitrophenyl, C 1 -C 4 alkylphenyl, C 8 alkoxyphenyl C 1 -C 4 alkoxy, naphthyl, cyanonaphthyl, nitronaphthyl, halo-naphthyl, C 1 -C 4 -alkyl-naphthyl, C 1 -C 4 -alkoxy-naphthyl, phenylalkyl C6 alkyl or naphthyl-C 1 -C 6 alkyl, and the radicals R ¹³ and R ^{X 4} independently of one another are hydrogen, alkyl having 1 to 6 carbon atoms, an alkylcarbonyl group having 2 to 6 C carbon, phenyl, halophenyl, cyanophenyl, nitrophenyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkoxyphenyl, naphthyl, cyanonaphthyl, nitronaphthyl, halogenated naphthyl, C 1 -C 4 alkylnaphthyl or alkoxynaftylovú having 1 -C 4 alkoxy; R ² and R ³ independently of one another are hydrogen, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 6 carbon atoms which is substituted by halogen, cyano, nitro, C 1 -C 8 alkoxy, phenyl, naphthyl, phenoxy, naphthoxy, phenyl substituted with halogen, cyano, nitro, -OR ^S , -NR ^XO R ^XX or -CONR ^S R ® , naphthyl substituted with halogen, cyano, nitro, —OR ^S, -NR ^XX R ^XO or CONR ^e R ^9, phenoxy which is substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{XO XX} or -CONR ^e R®, naftoxyskupi9 Nou, which is substituted by halogen, cyano, nitro, -OR ^3, -NR R ^{XO and XX} or CONR R®, alkylthio having 1 to 8 carbon atoms, phenylthio, naphthylthio, phenylthio which is substituted by halogen, cyano, nitro, -0R ^s, - DB ^XO R ^XX or -CONR ^e R®, naphthylthio which is substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{XO and XX} or CONR R®, trialkylsilyl having 3 to 6 carbon atoms, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium, C 2 -C 8 alkoxycarbonyl, carboxyl, -COOM, where M is ammonium or an alkali metal atom or an alkaline earth metal atom, or a C 3 -C 8 cycloalkyl group, a C 2 -C 5 alkylcarbonyloxy group, a phenylcarbonyloxy group, a naphthylcarbonyloxy group, a C 1 -C 6 alkylamino group, a C 2 -C 5 alkylcarbonyl group or a dialkyl The radicals R @ ¹² and R @ ² and R @ ³ each independently represent a C2 -C6 alkenyl group, a C2 -C6 alkenyl group which is substituted by halogen, cyano, nitro or C1 -C8 alkoxy. , phenoxy, naphthoxy, phenoxy substituted with halogen, cyano, nitro, -OR ³ , -NR ^XO R ^XX or -CONR ^and R ⁹ , naphthoxy substituted with halogen, cyano, nitro,

-OR ³ , -NR ^XO R ^XX or -CONR ^and R ⁹ , C 1 -C 8 alkylthio, phenylthio substituted with halogen, cyano, nitro, -OR ³ , -NR ¹⁰ R ¹ or -CONR ^and R 9 ^9, naphthylthio which is substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{XO X 1} or CONR ⁹ R ^s, trialkyl10 silyl group having 3 to 6 carbon atoms, hydroxyl, amino, ammonium-tri-C 1 up to 4 carbon atoms in each alkyl moiety, C 2 -C 8 alkoxycarbonyl, carboxyl, -COOM, where M is an ammonium or alkali metal or alkaline earth metal atom, or a C 3 -C 8 cycloalkyl group, (C 2 -C 5) alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, (C 1 -C 6) alkylamino, (C 2 -C 5) alkylcarbonyl or C 2 -C 12 dialkylamino, or R ² and R ³ independently represent C 2 -C 6 alkynyl, C 2 -C 6 alkynyl which is substituted by halogen, cyano, nitro, alkoxy C 1 -C 8, phenoxy, naphthoxy, C 1 -C 8 alkylthio, phenylthio, naphthylthio, phenoxy substituted with halogen, cyano, nitro, -OR ^S , -NR ^XO R ^XX or -CO NR ^and R ⁹ , naphthoxy which is substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^XX and ^XO -C0NR ^and R ^9, phenylthio which is substituted by halogen, cyano, nitro, -0R ^a, -NR ^XX R ^XO or -CONR ^and R ⁹ , naphthylthio which is substituted by halogen, cyano, nitro, -OR ^S , -NR ^XO R ^XX or -CONR ^e R ®, trialkylsilyl group C 3 -C 6 pins, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium, C 2 -C 8 alkoxycarbonyl, carboxyl, -COOM, where M is ammonium or an alkali metal or alkaline earth metal atom, or a C 3 -C 8 cycloalkyl group, or R ² and R ^{3 are} each independently a formyl group, a C 2 -C 15 alkylcarbonyl group, a C 2 -C 15 alkenylcarbonyl group C 4 -C 9 cycloalkylcarbonyl, C 6 -C 9 cycloalkenylcarbonyl or C 3 -C 8 cycloalkylalkylcarbonyl and C 2 -C 6 alkylcarbonyl, which may be halogen, cyano nitro, hydroxy, amino C 1 -C 6 alkylamino, C 2 -C 12 dialkylamino, carboxyl, -COOM, wherein M is an ammonium or alkali metal or alkaline earth metal atom, or a C 2 -C 8 alkoxycarbonyl group , C 4 -C 10 cycloalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl or C 3 -C 12 dialkylaminocarbonyl, or R ² and R ³ each independently represent a heterocyclyl group, a heterocyclylcarbonyl group, a heterocyclyl group, a heterocyclyl group is substituted with halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkylcarbonyloxy, C 2 -C 6 alkoxycarbonyl , aminocarbonyl, and (C 2 -C 6) alkylamino or (C 3 -C 11) dialkylaminocarbonyl, or a heterocyclylcarbonyl substituted with halogen, cyano, nitro, (C 1 -C 5) alkyl, (C 1 -C 5) alkoxy, (C 1 -C 5) alkylcarbonyl (C 2 -C 5) alkoxycarbonyl, (C 2 -C 6) alkoxycarbonyl, (C 2 -C 6) amino12 cartonyl, (C 2 -C 6) alkylamino or (C 2 -C 5) alkylcarbonyloxy, or R ² and R ³ independently represent phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenylalkylcarbonyl having 2 to 6 carbon atoms in the alkylcarbonyl moiety, biphenylcarnonyl having 2 to 6 carbon atoms in the alkylcarbonyl moiety, naphthylalkylcarbonyl having 2 to 6 carbon atoms in the alkylcarbonyl moiety, and phenylcarbonyl; 6 to 6 carbon atoms in the alkenylcarbonyl moiety, biphenylalkenylcarbonyl having 3 to 6 carbon atoms in the alkenylcarbonyl moiety, naphthylalkenylcarbonyl having 3 to 6 carbon atoms in the alkenylcarbonyl moiety, phenylalkinylcarbonyl having 3 to 6 carbon atoms in the 3-C6 alkynyl carbonyl moiety; C 3 -C 6 alkynylcarbonyl or C 3 -C 6 naphthylalkynylcarbonyl, which may be substituted by C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylthio, haloalkyl (C 1 -C 5) alkyl, (C 2 -C 5) alkylcarbonyl, halogen, cyano, amino, nitro, carboxyl, (C 2 -C 8) alkoxycarbonyl, hydroxy, (C 2 -C 8) alkylaminocarbonyl 6 or C 2 -C 12 dialkylaminocarbonyl, or R ² and R ^{3 are} each independently C 1 -C 6 alkyl, C 1 -C 6 biphenylalkyl, naphthylalkyl (C 1 -C 6) alkyl, phenylalkenyl (C 2 -C 6) alkenyl, biphenylalkenyl (C 2 -C 6), naphthyl (C 2 -C 6) alkenyl, phenylalkinyl (C 2 -C 6) alkynyl, (C 2 -C 6) biphenylalkynyl or (C 2 -C 6) naphthylalkynyl which may be substituted with (C 1 -C 5) alkyl, alkenyl C 2 -C 5 alkynyl; C 2 -C 5 alkynyl C 1-4 alkoxy, hydroxy, C 1 -C 5 alkoxy, formyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 9 dialkylaminocarbonyl or C 2 -C 3 alkylthio or C 1 -C 5 alkylthio or R ² and R ^{3 are} each independently phenyl, naphthyl or heterocyclyl, which groups may be substituted by halogen, cyano, nitro, C 1 -C 5 alkyl C 5 -C 5 alkoxy, C 1 -C 5 alkoxy, C 1 -C 5 alkylthio, carboxyl, -CONH _a , C 2 -C 6 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 2 -C 2 alkylcarbonyl up to 5 carbon atoms or alkoxycarbonyl C 2 -C 5, or R ² and R ³ together with the nitrogen atom to which they are attached, form a heterocyclic ring which may be substituted by C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halo, cyano or nitro or R @ ² and R @ ^{3 are} each independently amino, C1 -C6 alkylamino, C2 -C8 dialkylamino, phenylamino, naphthylamino, C2 -C6 alkylcarbonylamino, alkoxycarbonylamino; (2-10 carbon atoms), hydroxy, (1-6C) alkoxy, (2-6C) alkylcarbonyloxy, phenoxy, biphenyloxy or naphthoxy,

X is O or S (O) _x , wherein x is 0, 1 or 2, and

R ⁴ represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkynyl group having 2 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 5 to 8 carbon atoms, a cycloalkylalkyl group C 3 -C 8 cycloalkyl and C 1 -C 4 alkyl or C 1 -C 4 alkylcycloalkyl C 3 -C 8 cycloalkyl, which groups may be substituted by halogen, cyano, nitro, oxo or -OR ^S , or

R ⁴ represents a phenyl group, a naphthyl group, a heterocyclyl group, an alkylphenyl group having 1 to 4 carbon atoms in the alkyl moiety, an alkylnaphthyl group having 1 to 4 carbon atoms in the alkyl moiety, a phenylalkyl group having 1 to 4 carbon atoms in the alkyl moiety C 1 -C 4 alkyl, which groups may be substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 4 alkylthio C 1 -C 10 haloalkyl, C 1 -C 10 haloalkoxy, C 1 -C 10 haloalkylthio, C 3 -C 10 alkoxycarbonylalkoxy, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl C1-6 alkyloxycarbonyl; C 2 -C 6 -alkyl, C 2 -C 6 -alkylcarbonyl, -CONH ₂ , formyl, C 2 -C 7 -alkylaminocarbonyl, C 3 -C 11 -alkylaminocarbonyl, C 3 -C 6-trialkylsilyl carbon, C 2 -C 10 alkylcarbonylamino, C 2 -C 10 alkylcarbonyloxy, phenoxy, halophenoxy, pyridyloxy or pyridyloxy substituted with halo, C 1 -C 4 alkyl, alkoxy, nitro or amino, or two adjacent substituents on the phenyl or naphthyl ring R ⁴ form a carbocyclic or heterocyclic ring, which may be substituted by halogen, cyano, nitro, amino, carboxyl, oxo, C 1 -C 10 alkyl, C 1 -C 10 alkyloxy (C 1 -C 10) alkylthio, (C 1 -C 10) alkylthio, (C 1 -C 10) haloalkyl, hydroxy, (C 3 -C 10) alkoxycarbonylalkoxy, (C 1 -C 6) alkylsulfinyl, (C 1 -C 6) alkylsulfonyl, (C 2 -C 6) alkoxycarbonyl, (C 2 -C 6) alkylcarbonyl, -CONH ₂ , formyl, C 2 -C 7 alkylaminocarbonyl, C 3 -C 11 dialkylaminocarbonyl, C 3 -C 3 trialkylsilyl 6 carbon atoms, C 2 -C 10 alkylcarbonylamino, C 2 -C 10 alkylcarbonyloxy, phenoxy, pyridyloxy or pyridyloxy substituted with halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, nitro or amino, and salts the compounds of formula I, with the exception of the compounds of formulas I, Ia, Ia _2, ^{Ia, and N,} and

NH,

NH,

S-CH.

(Ia),

N //

H _{3 EN} N (Ia _t ),

O-phenyl

NH,

N π-CxHq-S ^ N

NH, / N \ (a-,), Cl (CH _{2) 4} - p \ _(I-3) and

O-phenyl

0fenyl

(I and j.

The invention also relates to compounds of formula I

NF ^ ^R3

In which

R ^x is C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl C 1 -C 17 alkyl, C 1 -C 17 alkylcycloalkyl C 3 -C 8 alkyl, C 2 -C 17 alkenyl, C 3 -C 8 cycloalkylalkenyl and C 2 -C 17 alkenyl, C 2 -C 17 alkenylcycloalkyl C 3 -C 8 alkenyl C 3 -C 8 alkynyl, C 2 -C 17 alkynyl, C 3 -C 8 cycloalkylalkynyl C 2 -C 17 alkynyl, C 2 -C 17 alkynylcycloalkyl carbon atoms in the alkynyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, cycloalkenes C 5 -C 8 -cycloalkenylalkyl having 5 to 8 carbon atoms in the cycloalkenyl moiety and 1 to 17 carbon atoms in the alkyl moiety, alkylcycloalkenyl having 1 to 17 carbon atoms in the alkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety C 5 -C 8 cycloalkenylalkenyl having 2 to 17 carbon atoms in the alkenyl moiety, C 2 -C 17 alkenyl cycloalkenyl having 5 to 8 carbon atoms in the cycloalkenyl moiety, C 5 -C 8 cycloalkenylalkinyl 8 carbon atoms in the cycloalkenyl moiety and 2 to 17 carbon atoms in the alkynyl moiety, alkynylcycloalkenyl group having 2 to 17 carbon atoms in the alkynyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkylcycloalkyl of 3 to 8 carbon atoms in each cycloalkyl moiety cycloalkenylcycloalkenyl of 5 to 8 carbon atoms; in each cycloalkenyl moiety, cycloalkylcycloalkenyl of 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylcycloalkyl of 5 to 8 carbon atoms in the cycloalkenyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety C 2 -C 17 alkynyl and C 2 -C 17 alkenyl or C 2 -C 17 alkenyl-C 2 -C 17 alkynyl, which groups may be halogen-substituted, cyano, nitro, oxo, -OR ⁵ , -S (O) R ⁶ , n

—COOR ⁷ , -CONR ^e R®, -NR ^XO R ^XX , = NR ^{X 2} , = N-NR ¹³ R 2 ^L ' ¹ , phenyl, biphenyl, naphthyl or heterocyclyl, the phenyl, naphthyl and heterocyclyl substituents can be unsubstituted or substituted by halogen, cyano, nitro, -OR ⁵ , -NR ^XO R ^XX or -CONR ^and R ⁹ , or

R ¹ represents a heterocyclyl group, the heterocycle being attached to the thiatriazine ring through one of its carbon atoms and wherein the heterocycle may be substituted by halogen, cyano, nitro, oxo, -OR ⁵ , -S (O) R ®, -COOR ⁷ , n

-CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ^{X 2} , = N-NR ^{X 3} R ^X *, C 1 -C 17 alkyl, C 2 -C 17 alkenyl, C 2 -C 17 alkynyl C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, phenyl, biphenyl, naphthyl, C 1 -C 17 alkyl substituted with halogen, cyano, nitro, -OR ^S , -CONR®R ⁹ or -NR ^XO R ^XX , a C 2 -C 17 alkenyl substituted with halogen, cyano, nitro, -OR ^S , -CONR ® R ⁹ or -NR ^XO R ^XX , alkynyl group having 2 to 17 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, cycloalkyl having 3 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^p , -CONR ^a R ⁹ or -NR ^XX R ^XO, cycloalkenyl of 5-8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, phenyl which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, biphenyl which is substituted by halogen, cyano, nitro, -0R ^{s, 9} or -CONR®R ^XO -NR R ^11, or naphthyl which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, or

R ^x represents phenyl, biphenyl, naphthyl, C 1 -C 10 alkylphenyl, C 1 -C 10 alkylbiphenyl, C 1 -C 10 alkylnaphthyl, C 1 -C 10 alkenylphenyl C 2 to C 10 alkenyl, C 2 to C 10 alkenyl, C 2 to C 10 alkenyl, naphthyl, C 2 -C 10 alkynyl, C 2 -C 10 alkynyl C 10 alkynyl or C 2 -C 10 alkynyl-naphthyl which may be substituted with h 2 OO logene, cyano, nitro, -OR ^S , -S (O) R ^e , -COOR ⁷ , - CONR ^e R ® or -NR ¹⁰ R ^X1 , wherein

Π

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 7 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino carbon atoms, -N = CH ₂ , -N = CH-alkyl of 1 to 4 carbon atoms in the alkyl moiety, -N = C (alkyl) ₂ of 1 to 4 carbon atoms in each alkyl moiety, trialkylsilyl C3 -C6 cycloalkyl, C3 -C7 cycloalkyl, C2 -C7 alkenyl or C3 -C7 alkynyl, n has the value 0, 1, or 2

R ⁶ represents a hydrogen atom or a cyano group when n is 0, or

R ^e represents a C 1 -C 5 alkyl group, a C 1 -C 5 haloalkyl group, a C 1 -C 5 hydroxyalkyl group, a phenyl group, a naphthyl group, an alkylphenyl group of 1 to 4 carbon atoms in the alkyl moiety, an alkylnaphthyl group (C 1 -C 4) -alkyl, halogen-phenyl, halo-phenyl, heterocyclyl, halogen-heterocyclyl or (C 3 -C 7) -cycloalkyl,

R ⁷ is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 6 nitroalkyl, C 1 -C 6 cyanoalkyl, phenyl, naphthyl, halophenyl , halo-phenyl, C 2 -C 10 alkoxyalkyl, C 1 -C 10 alkylcarbonyl, heterocyclyl, halo-heterocyclyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halo-cycloalkyl-N, CH _2, N = CH-C 1 -C 4 alkyl, a group -N = C (alkyl) ₂ having 1 to 4 carbon atoms, alkylamino or dialkylamino having 2 to 6 carbon atoms; R ^s and R ⁹ are each independently hydrogen, phenyl, naphthyl, halophenyl, halophthyl, alkyl with 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, phenoxy, naphthoxy, halophenoxy, halo-phenoxy, cyanoalkyl of 1 to 7 carbon atoms, alkynyl of 3 to 8 carbon atoms a C 7-C group or a C až-C alko alkoxyalkyl group, or R® and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated, R ⁱ and R ¹¹ independently are each hydrogen, phenyl, naphthyl, halophenyl, halophthyl, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, phenoxy, haloxy, halo, cyanoalkyl of 1 to 7 carbon atoms, alkenyl of 3 to 7 carbon atoms (C,-C alk) alkynyl, (C až-C alk alk) alkynyl, (C až-C alko alko) alkoxyalkyl, (C až-C alky) alkylamino, (C až až dial) dialkylamino, formyl, (C až-C alkyl) alkylcarbonyl, phenylcarbonyl or naphthylcarbonyl, wherein the phenyl or naphthyl radical in these groups may be substituted by a C1 -C4 alkyl, halogen, C1 -C4 alkoxy, hydroxy, cyano, nitro or C1 -C6 alkoxycarbonyl radical; or the radicals R ^x and R ¹¹ together with the nitrogen to which they are attached form heterocycle, which may be halogenated,

R ¹² represents a hydrogen atom, a C 1 -C 8 alkyl group, a C 1 -C 8 haloalkyl group, a phenyl group, a halophenyl group, a cyanophenyl group, a nitrophenyl group, a C 1 -C 4 alkylphenyl group, an alkoxyphenyl group C 1 -C 4 alkoxy, naphthyl, cyanonaphthyl, nitronaphthyl, halogenaphthyl, C 1 -C 4 alkylnaphthyl, C 1 -C 4 alkoxynaphthyl, phenylalkyl and R @ ¹³ and R @ ¹⁴ are each independently hydrogen, (C1 -C6) alkyl, (C1 -C6) alkyl (C1 -C6) alkyl or naphthylalkyl (C1 -C6); carbon atoms, phenyl, halophenyl, cyanophenyl, nitrophenyl, C 1-4 alkylphenyl, C 1-4 alkoxyphenyl, C 1-4 alkoxy, naphthyl, cyanonaphthyl, nitronaphthyl, halogenaphthyl, C 1-4 alkylnaphthyl R ² and R ^{3 are} each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with halogen or C 1 -C 4 alkoxynaphthyl; , cyano, nitro, C 1 -C 8 alkoxy, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium, carboxy, -COOM, wherein M represents an ammonium group or an alkali metal atom or a k atom alkaline earth or C 3 -C 8 cycloalkyl, C 1 -C 5 alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C 1 -C 6 alkylamino, C 1 -C 5 alkoxycarbonyl, dialkylamino , phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, bifenyloxyskupinou, phenylthio or naphthylthio, and these aromatic rings may be unsubstituted or substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{1 O 1: L,} alkyl (C 4-C 4), formyl, (C až-C alkyl) alkylcarbonyl, COOR ⁷ , (C až-C alkyl) alkylthio, (C až-C alkyl) alkylsulfonyl or CONR ^and R R, or R ² and R ³ independently represent an alkenyl group C 2 -C 6 alkenyl, C 2 -C 6 alkenyl substituted with halogen, cyano, nitro, C 1 -C 8 alkoxy, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium a (C 1 -C 4) trialkylammonium group in each alkyl moiety, a carboxyl group, a -COOM group wherein M is an ammonium or alkali metal or alkaline earth metal atom, or a C 3 -C 8 cycloalkyl group, C 5 -C 5, phenylcarbonyloxy, naphthylcarbonyloxy, C 1 -C 6 alkylamino, C 2 -C 5 alkoxycarbonyl, C 2 -C 12 dialkylamino, phenyl, naphthyl, phenoxy, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, biphenyl, naphthylthio, pri wherein these aromatic rings may be unsubstituted or substituted by halogen, cyano, nitro, -OR ^S , -NR ^XO R ^XX , C 1 -C 4 alkyl, formyl, C 1 -C 4 alkylcarbonyl, COOR · ⁷ , alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, or CONR ^and R ⁽ R ⁾ , or R ( ²⁾ and R ( ³⁾ independently of each other are alkynyl of 3 to 6 carbon atoms, alkynyl of 3 up to 6 carbon atoms which is substituted by halogen, cyano, nitro, C1-C8alkoxy, C3-C6-trialkylsilyl, hydroxy, amino, ammonium, C1-C4-trialkylammonium in each alkyl moiety , a carboxyl group, a -COOM group, wherein M represents an ammonium group or an alkali metal atom or a metal atom alkaline earth or C 3 -C 8 cycloalkyl, C 1 -C 5 alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyl 25 oxy, C 1 -C 6 alkylamino, C 1 -C 5 alkoxycarbonyl, C 2 -C 12 dialkylamino , phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenylthio or naphthylthio, the aromatic rings may be unsubstituted or substituted by halogen, cyano, nitro, -OR ⁵ , -NR ¹⁰ R ¹¹ C 1-4 alkylcarbonyl, C 1-4 alkylcarbonyl, COOR ⁷ , C 1-4 alkylthio, C 1-4 alkylsulfonyl or CONR ^e R ⁹ , or R ² and R 4 ³ independently represent a formyl group , (C 1 -C 15) alkylcarbonyl, (C 2 -C 15) alkenylcarbonyl, (C 4 -C 9) cycloalkylcarbonyl, (C 6 -C 9) cycloalkenylcarbonyl or C 3 -C 8 cycloalkylalkylcarbonyl group in the cycloalkyl portion up to 6 carbon atoms in the alkyl moiety, which groups may be substituted by halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 alkylamino, C 2 -C 12 dialkylamino, carboxyl, -COOM, wherein M is an ammonium or alkali metal or alkaline earth metal atom, or a C 1 -C 8 alkoxycarbonyl group, a C 4 -C 10 cycloalkoxycarbonyl group, a C 1 -C 8 alkylaminocarbonyl group or a C 2 -C 12 dialkylaminocarbonyl group, or symbol R ² and R ^{3 are} each, independently, heterocyclyl, heterocyclylcarbonyl, heterocyclyl substituted with halogen, cyano, nitro, (C 1 -C 5) alkyl, (C 1 -C 5) alkoxy, (C 1 -C 5) alkylcarbonyl C 1 -C 5 alkylcarbonyloxy, C 1 -C 6 alkoxycarbonyl, aminocarbonyl, C 1 -C 6 alkylaminocarbonyl or C 2 -C 11 dialkylaminocarbonyl, or a heterocyclylcarbonyl group which is a halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, aminocarbonyl, C 1 -C 6 alkylamino carbon atoms but will alkylcarbonyloxy having 1 to 5 carbon atoms, or the radicals R ² and R ³ independently of one another are phenylcarbonyl, bifenylkarbonylovú group, naphthylcarbonyl, fenylalkylkarbonylovú having 1 -C 6 alkyl, bifenylkarbonylovú having 1 to 6 carbon atoms in the alkyl moiety, naphthylalkylcarbonyl of 1 to 6 carbon atoms in the alkyl moiety, phenylalkenylcarbonyl of 2 to 6 carbon atoms in the alkenyl moiety, biphenylalkenylcarbonyl of 2 to 6 carbon atoms in the alkenyl moiety, naphthylalkenylcarbonyl of the 2 to 6 carbon atoms phenylalkynylcarbonyl having 3 to 6 carbon atoms in the alkynylcarbonyl moiety, biphenylalkynylcarbonyl having 3 to 6 carbon atoms in the alkynylcarbonyl moiety or naphthylalkynylcarbonyl having 3 to 6 carbon atoms in the alkynylcarbonyl moiety, which groups may be substi C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, C 1 -C 5 -alkylthio, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkylcarbonyl, halogen, C 1-4 alkyl, amino , nitro, -COOR ⁷ , C 1 -C 8 alkoxycarbonyl, hydroxy, C 1 -C 5 alkylsulfinyl, C 1 -C 5 alkylsulfonyl, C 1 -C 6 alkylaminocarbonyl or C 2 dialkylaminocarbonyl up to 12 carbon atoms or R ² and R ^{3 are} each independently phenyl, naphthyl or heterocyclyl, which may be substituted by halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkyl C 1 -C 5 alkylthio; ka, carboxyl, -CONH _2, an alkylaminocarbonyl group having 1 to 6 carbon atoms, dialkylaminocarbonyl group having 2 to 10 carbon atoms, alkylcarbonyl having 1 to 5 carbon atoms or alkoxycarbonyl having 1 to 5 carbon atoms, or ^two radicals R and R ³ together with the nitrogen atom to which they are attached form a heterocyclic ring which may be substituted with a C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halogen, cyano or nitro group, or R ² and R 3 ^{3 are,} independently of one another, amino, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, phenylamino, naphthylamino, C 1 -C 6 alkylcarbonylamino, C 1 -C 10 alkoxycarbonylamino, hydroxy 1, (C 1 -C 6) alkylcarbonyloxy, phenoxy a group, biphenyloxy or naphthoxy,

X represents an oxygen atom or a S (O) _x group wherein x is 0, 1 or 2, and

R ⁴ represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkynyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 5 to 8 carbon atoms, a cycloalkylalkyl group (C 3 -C 8) cycloalkyl and (C 1 -C 4) alkyl or (C 1 -C 4) alkyl (C 3 -C 8) cycloalkyl group, which groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo or ^a group -0R, or

R ⁴ represents a phenyl group, a biphenyl group, a naphthyl group, a heterocyclyl group, an alkylphenyl group having 1 to 4 carbon atoms in the alkyl moiety, an alkylnaphthyl group having 1 to 4 carbon atoms in the alkyl moiety, a phenylalkyl group having 1 to 4 carbon atoms in the alkyl moiety or naphthylalkyl having 1 to 4 carbon atoms in the alkyl moiety, which groups may be unsubstituted or substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms , (C 1 -C 6) alkylamino, (C 2 -C 8) dialkylamino, (C 1 -C 10) alkylthio, (C 1 -C 10) haloalkyl, (C 1 -C 10) haloalkoxy (C 1 -C 10) alkoxycarbonyl alkoxy having 2 to 10 u atoms hlíka, alkylsulfinyl of 1 to 6 carbon atoms, the alkylsulfonyl group to 6 carbon atoms, an alkyloxycarbonyl group having 1 to 6 carbon atoms, alkylcarbonyl having 1 to 6 carbon atoms, -CONH _2, formyl skúpi29 Nou, alkylaminocarbonyl with 1 C 7 -C 10 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl, C 1 -C 10 alkylcarbonylamino, C 1 -C 10 alkylcarbonyloxy, phenoxy, halophenoxy, pyridyloxy or pyridyloxy; halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, cyano, nitro or amino, or two adjacent substituents on the phenyl or naphthyl ring R ⁴ form a carbocyclic or heterocyclic ring which may be substituted by halogen, cyano pin, nitro, amino, carboxyl, oxo, C 1 -C 10 alkyl, C 1 -C 10 alkyloxy, C 1 -C 10 alkylthio, C 1 -C 10 haloalkyl, hydroxy, C 3 -C 3 alkoxycarbonylalkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, -CONH 4, formyl, alkylaminocarbonyl (C 2 -C 7), (C 3 -C 11) dialkylaminocarbonyl, (C 3 -C 6) trialkylsilyl, (C 2 -C 10) alkylcarbonylamino, (C 2 -C 10) alkylcarbonyloxy, phenoxy, pyridyloxy or pyridyloxy group substituted with halogen, alkyls (C 1 -C 4), C 1 -C 4 -alkoxy, cyano, nitro or amino, and salts of the compounds of formula (I), with the exception of the compounds of formulas Ia, Ia, Ia, Xa ₃ and Ia

NH,

NH,

CH ₃ CH ₂ - SN ^N W

.., H, CS N (1 a), ³ \ /

N = <

G ^and i)>

N w // NS n C ₄ H _g - SNN = <

S-CK, nh ₂

O-phenyl

NH,

N x v / x (Ia ₂ ), CI (CH ₂ ) ₄ -N

N = <

(Ia ₃ ) a

O-phenyl

NH,

O-phenyl]

H, CS N ^x / N = <

(A,) ·

O-CH ₃

The alkyl groups in the substituent definitions may be straight-chain or branched and include, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl or octadecyl or e-octosecyl groups. isomers of these groups. Alkoxy, alkenyl and alkynyl groups are derived from the above alkyl groups. Alkenyl and alkynyl groups may be unsaturated one or more times.

Suitable cycloalkyl groups contain 3 to 8 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl groups. The corresponding cycloalkenyl groups may be unsaturated one or more times, for example cyclopentadienyl or cyclooctatetraenyl.

When an alkyl, alkenyl or alkynyl group is present as a substituent on a cycloalkyl, cycloalkenyl, phenyl, biphenyl, naphthyl or heterocyclyl group, these ring systems may also be polysubstituted with alkyl, alkenyl or alkynyl groups.

Halogen is generally fluorine, chlorine, bromine or iodine. This also applies to halogens in conjunction with other meanings, such as haloalkyl or halophenyl.

Heterocyclyl groups are to be understood as meaning ring systems which, in addition to the carbon atoms, contain at least one heteroatom such as nitrogen, oxygen and / or sulfur. They may be saturated or unsaturated. These ring systems preferably contain 3 to 9 ring atoms. This also applies to heterocycles which consist of two substituents attached to a nitrogen atom, as is the case with groups such as -NR ^XO R ^1X .

Preferred R ¹ heterocycles that are suitable are, for example, oxiranyl, dioxolanyl, dioxanyl, 2,3-dihydro [1,4] dioxinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, pyridinyl, pyrimidinyl, imidazolyl, imidazolyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydropyranyl, tetrahydropyranyl, tetrahydropyranyl, tetrahydropyranyl, tetrahydropyranyl dihydrofuranyl, thiophenyl, 2,3-dihydrothiophenyl, tetrahydrothiophenyl and dihydropyranyl.

Heterocyclyl as a substituent of R ^x may be, for example, oxiranyl, dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyridinyl, imidazolyl, tetrahydrofuranyl, tetrahydropyranyl, dihydrofuranyl, dihydropyranyl or phthalimidyl.

Heterocycles as defined by R® are preferably, inter alia, pyridinyl, pyrimidinyl and triazinyl.

Preferred heterocycles in R ⁷ are, for example, oxetanyl, pyridyl, thiophenyl and furanyl.

R @ ^a and R @ ⁹ preferably form rings such as piperidinyl, morpholinyl and pyrrolidinyl.

Preferred examples of heterocycles formed by R ^xo and R ^xx or R ² and R ³ , together with the nitrogen atom to which they are attached, are piperidinyl, morpholinyl, pyrrolidinyl and imidazolyl.

R ⁹ heterocycles are preferably thiophenyl, furanyl, pyridinyl and oxetanyl.

The R ⁴ phenyl and naphthyl rings may be substituted by carbocyclic or heterocyclic radicals, which are formed by two adjacent substituents of these phenyl or naphthyl rings. The carbocyclic radicals preferably contain from 4 to 6 carbon atoms, such as cyclobutyl, cyclopentyl and cyclohexyl.

Preferred heterocyclic groups are especially dioxolanyl and tetrahydrofuranyl.

Carbocyclic groups, such as phenyl or cyclohexenyl, may be fused to heterocycles R ⁴ , such as succinimidyl, pyridinyl, thiophenyl or furanyl groups.

Heterocycles R ² and R ³ are preferably pyridinyl, pyrrolidinyl and pyrimidinyl.

N-R ² R ³ heterocycles include, for example, succinimidyl, imidazolyl and triazolyl groups, and carbocyclic radicals such as phenyl or cyclohexenyl may be fused to these groups.

A heterocyclylcarbonyl group R ² or R ³ is, for example, pyridinyl, pyrrolidinyl, triazolyl, thiophenyl, furanyl or isoxazolyl.

In substituents such as the group -N = C (alkyl) ₂ with 1 to 4 carbon atoms in each alkyl moiety, the alkyl moieties may be the same or different. Preferably these residues are the same. This also applies to the alkyl radicals in the dialkylamino group, the dialkylaminocarbonyl group, the trialkylammonium group and the trialkylsilyl group.

In the definitions of cyanoalkyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl, alkylcarbonylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonylalkoxy and alkenylcarbonyl groups, the carbon atom at each carbon atom and the carbon atom at each carbon atom within each carbon atom.

Suitable alkali and alkaline earth metals are, for example, lithium, sodium, potassium, magnesium, calcium or barium.

The invention also includes the salts which the compounds of formula (I) may form, in particular with amines, alkali metal bases, alkaline earth metal bases or quaternary ammonium bases.

In particular, the salt-forming compounds of the group of alkali metal hydroxides and alkaline earth metal hydroxides are lithium, sodium, potassium, magnesium or calcium hydroxides or, in particular, sodium or potassium hydroxides.

Examples of amines suitable for forming ammonium salts include ammonia as well as primary, secondary and tertiary C 1 -C 18 alkylamines, C 1 -C 4 hydroxyalkylamines and C 2 -C 4 alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four butylamine isomers, n-amyl amine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamino, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhecylamino, metylnonylamín, metylpentadecylamín, metyloktadecylamín, ethylbutylamine, etylheptylamín, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, propanolamine, ethanolamine, ethanolamine, ethanolamine, ethanolamine, ethanolamine, ethanolamine diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butene yl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tris-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine, heterocyclic amines, e.g. for example, anilines, methoxyanilines, ethoxyamnilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines, but especially triethylamine, isopropylamine and diisopropylamine.

The compounds of formula I contain a center of asymmetry at the sulfur atom in the thiatriazine ring. Therefore, in the preparation of these compounds racemates are obtained which can be separated into the corresponding enantiomers by conventional separation methods. If the thiatriazine ring substituents contain additional centers of symmetry, it is also possible to separate the corresponding diastereoisomers in a conventional manner. The invention also encompasses such diasteroisomers and enantiomers.

In preferred compounds of the invention

R ¹ represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkylalkyl group having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 17 carbon atoms in the alkyl moiety, alkylcycloalkyl having 1 to 17 carbon atoms C 3 -C 8 alkyl, C 2 -C 17 alkenyl, C 3 -C 8 cycloalkyl and C 2 -C 17 alkenyl, C 2 -C 17 alkenylcycloalkyl C3-C8 alkenyl, C3-C8 alkynyl, cycloalkylalkynyl and C2-C7 alkynyl, C2-C7 alkynylcycloalkyl and C3-C8 alkynyl carbon in the cycloalkyl moiety, a cycloalkenyl group of 5 to 8 atoms C 5 -C 8 cycloalkenylalkyl having 1 to 17 carbon atoms in the alkyl moiety, C 1 -C 17 alkylcycloalkenyl having 5 to 8 carbon atoms in the cycloalkenyl moiety, C 5 -C 8 cycloalkenylalkenyl the cycloalkenyl and 2 to 17 carbon atoms in the alkenyl moiety, the alkepin having a 2 to 17 C 3 -C 8 nylcycloalkenyl moiety in the alkenyl moiety and the 5 to 8 carbon atoms in the cycloalkenyl moiety, the cycloalkenylalkinyl group with 5 up to 8 carbon atoms in the cycloalkenyl moiety and 2 to 17 carbon atoms in the alkynyl moiety, alkynylcycloalkenyl of 2 to 17 carbon atoms in the alkynyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, a cycloalkylcycloalkyl group of 3 to 8 carbon atoms in each cycloalkyl moiety C 5 -C 8 cycloalkenylcycloalkenyl and in each cycloalkenyl moiety, cycloalkylcycloalkenyl of 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylcycloalkyl of 5 to 8 carbon atoms in the cycloalkenyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety (C 2 -C 17) alkynyl-alkenyl or C 2 -C 17 alkenyl or (C 2 -C 17) alkenyl and C 2 -C 17 alkynyl, which groups may be halogen-substituted, cyano, nitro, oxo, -0R ^a group -S (0) R ^6, n

-COOR ⁷ , -CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ^{X 2} , = N-NR ^{X 3} R ^{X 4} , phenyl, biphenyl, naphthyl or heterocyclyl, wherein the phenyl, naphthyl and heterocyclyl substituents may be substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{XO XX} or CONR ^a R ^9, or

R ^x is heterocyclyl wherein the heterocycle is bonded to the thiatriazine ring via one of its carbon atoms and which heterocycle may be substituted by halogen, cyano, nitro, oxo, -0R ^the group -S (O) _n R ^e, - COOR ^7, CONR ^e R ^9, -NR ^XX R ^{XO, X 2} = NR, = N-NR ^{X 3 X 4} R, alkyl having 1 to 17 carbon atoms, alkenyl group having 2 to 17 carbon atoms, alkynyl group of 2 to C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, phenyl, biphenyl, naphthyl, C 1 -C 17 alkyl substituted with halogen, cyano, nitro, - ^the oR, CONR ^a R c or -NR ^X R ^XX °, alkenyl group having 2 to 17 carbon atoms which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX , alkynyl in groups of 2 to 17 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, cycloalkyl having 3 to 8 carbon atoms, which is substituted by halogen, cyano, , nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, cycloalkenyl of 5-8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^with, or -CONR®R ⁹ - ^{XO XX} NR R, phenyl which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX, biphenyl which is substituted by halogen, cyano, nitro, a group ^of -0R , -CONR®R ⁹ or -NR ^XO R ^XX or a naphthyl group which is substituted by halogen, cyano, nitro, -OR ^S , -CONR®R ⁹ , or -NR ^XO R ^XX or and R ^s , R ® , R ⁷ , R ®, R ⁹ , R ^x0 , R ^xx , R ^X2 , R ^X3 , R ¹⁴ and n have higher de Finished meaning.

In one group of preferred compounds of formula I

R ^x is C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkylalkyl and C 1 -C 17 alkyl, C 1 -C 17 alkylcycloalkyl C 3 -C 8 alkyl, C 2 -C 17 alkenyl, C 3 -C 8 cycloalkylalkenyl and C 2 -C 17 alkenyl, C 2 -C 17 alkenylcycloalkyl C 3 -C 8 alkenyl, C 2 -C 17 alkynyl, C 3 -C 8 cycloalkylalkynyl C 2 -C 17 alkynyl or C 2 -C 7 alkynylcycloalkyl 17 carbon atoms in the alkynyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, which groups may be substituted with halogen or -0R ^p, and R ^p is as defined above.

In another preferred group of compounds of formula I

R ^x is a non-aromatic heterocyclyl group, said ring being bonded to the thiatriazine ring via one of its carbon atoms and which heterocycle may be substituted by halogen, cyano, nitro, oxo, -0R ^the group -S (O) _n R ^a, -COOR ^7, -CONR ^e R ^9, -NR ^XX R ^XO, = NR ^12, = N-NR ^{X 3 X 4} R, alkyl having 1 to 17 carbon atoms, alkenyl group having 2 to 17 carbon atoms, alkynyl of 2 up to 17 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms, phenyl, biphenyl, naphthyl, alkyl of 1 to 17 carbon atoms substituted by halogen, cyano, nitro, -OR ^B, -CONR ⁹ R ^s, or -NR R ^{XO XX,} alkenyl group having 2 to 17 carbon atoms which is substituted by halogen, cyano, nitro, skúpi39 nou -0R ^a, -CONR ^a R ^9, or -N R ^XO R ^XX, alkynyl group having 2 to 17 carbon atoms which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ⁹ R ^S or -NR ^{V * * * *} R ° ^{X XX,} cycloalkyl of 3 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, cycloalkenyl of 5-8 carbon atoms, which is substituted by halogen, cyano, nitro, -OR ^S , -CONR ^and R ⁹ or -NR ^XO R ^1X , a phenyl group which is substituted with halogen, cyano, nitro, -OR ^S , -CONR ^and R ⁹ or -NR ^XO R ^XX , a biphenyl group which is substituted by halogen, cyano, nitro, ^-OR, -CONR ⁹ R ^s or NR ^{@ 1 O} R ^XX or naphthyl which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ^9, or -NR ^X ° R ^XX .

Within this group of compounds of formula I, particularly preferred are those compounds, wherein R ^x can be substituted by halogen, cyano, nitro, oxo, -OR ^S, S (0) R ^e, -COOR ^7, -CONR ^a R ⁹ , -NR ^X0 R ^XX , n

= NR ^{X 2} , = N-NR ^{X 3} R ¹⁴ , C 1 -C 17 alkyl, C 2 -C 17 alkenyl, C 2 -C 17 alkynyl, C 3 -C 8 cycloalkyl, cycloalkenyl having 5 to 8 carbon atoms, alkyl having 1 to 17 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ⁸ R ⁹ or -NR ^{X 1} R ^{1 O,} an alkenyl group having 2 to 17 carbon atoms which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, alkynyl group having 2 to 17 carbon atoms which is substituted by halogen, cyano, nitro, -0R ^p. CONR ^a R ⁹ or -NR ^1X R ^XO, cycloalkyl having 3 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, ^-OR, -CONR ^a R ⁹ or -NR ^X R ^XX ° or cycloalkenyl with 5 to 8 atomic 40 m angle ms, which is substituted by halogen, cyano, nitro, -0R ^with, or -NR ⁹ -CONR®R ^XO R ^XX.

In another group of particularly preferred compounds of formula I, R ² and R ^{3 are} each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with halogen, cyano, nitro, C 1 -C 8 alkoxy, phenyl, phenoxy, phenyl substituted with halogen, cyano, nitro, -OR ^S , -NR ^XO R ^XX or -CONR ^S R ®, halogen-substituted phenoxy, cyano , nitro, -OR ⁵ , -NR ^XO R ^XX or -COOR ^and R ⁹ , alkylthio of 1 to 8 carbon atoms, phenylthio, phenylthio substituted with halogen, cyano, nitro, -OR ⁵ , -NR ^XO R ^XX or CONR ^with R®, and the symbols R ² and R ³ independently of one another are alkenyl with 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon halogen substituted by halogen, cyano, nitro, C1-C8alkoxy, phenoxy, phenoxy substituted by halogen, cyano, nitro, -OR ⁵ , -NR ^XO R ^XX or -CONR ³ R ⁹ , (C 1 -C 8) alkylthio, phenylthio substituted with halogen, cyano, nitro, -OR ⁵ , -NR ^XO R ^XX or -CONR ^S R ®, or R ² and R ³ independently represent alkynyl (C 2 -C 6) alkynyl (C 2 -C 6) alkynyl substituted with halo, cyano, nitro, (C 1 -C 8) alkoxy, phenoxy, naphthoxy, (C 1 -C 8) alkylthio, phenylthio, phenoxy which is substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{1 O XX} or CONR ^a R ^9, phenylthio which is substituted by halogen , cyano, nitro, -OR ³ , -NR ^XO R ^XX or -CONR ^and R ⁹ , or R ² and R ^{3 are} each independently formyl, C 2 -C 15 alkylcarbonyl, C 2 alkenylcarbonyl (C až-C cyk) cycloalkyl, (C až-C 9) cycloalkylcarbonyl, (C až-C 9) cycloalkenylcarbonyl or (C až-C 8) cycloalkylalkylcarbonyl group and (C 2-C až) alkyl groups which may be substituted halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 alkylamino, C 2 -C 12 dialkylamino, carboxyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, having 2 to 8 carbon atoms or a dialkylaminocarbonyl group a (C až-Cinou) pin, or R a ³ and R ^heteroc each independently represent a heterocyclylcarbonyl group, or R ^{2 a} and R ³ each independently represent a phenylcarbonyl group, a (Clal-Ceny) phenylalkylcarbonyl group, phenylalkenylcarbonyl having 3 to 6 carbon atoms in the alkenylcarbonyl moiety or phenylalkinylcarbonyl having 3 to 6 carbon atoms in the alkynylcarbonyl moiety, which groups may be substituted by an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group (C 1 -C 5), (C 1 -C 5) haloalkyl, (C 2 -C 5) alkylcarbonyl, halogen, cyano, amino, nitro, carboxyl, (C 2 -C 8) alkoxycarbonyl, hydroxy, (C 2 -C 5) alkylaminocarbonyl up to 6 carbon atoms or or (C 2 -C 12) dialkylaminocarbonyl, or R ² and R ^{3 are} each independently C 1 -C 6 alkyl, C 2 -C 6 phenylalkenyl or C 2 -C 2 phenylalkenyl; C 2 -C 6 alkynyl, biphenylalkynyl C 2 -C 6 alkynyl which may be substituted with C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl carbon, hydroxy, C 1 -C 5 alkoxy, formyl, C 2 -C 6 alkylcarbonyl, C 2 -C 2 alkylaminocarbonyl, C 3 -C 9 dialkylaminocarbonyl, nitro or C 1 -C 6 alkylthio 5 carbon atoms or carbon atoms, up to 6 carbon atoms R ² and R ^{3 are} each independently phenyl or phenyl substituted with halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylthio43 ka, carboxyl, -CONH _a , alkylaminocarbonyl of 2 to 6 carbon atoms, dialkylaminocarbonyl of 3 to 10 carbon atoms, alkylcarbonyl of 2 to 5 carbon atoms or alkoxycarbonyl of 2 to 5 carbon atoms, or R ² and R ^{3 are} each independently amino, (C 1 -C 6) alkylamino, (C 2 -C 8) dialkylamino, phenylamino, (C 2 -C 6) alkylcarbonylamino, (C 2 -C 10) alkoxycarbonylamino, (C 1 -C 6) alkoxy C 6 -C 6 alkylcarbonyloxy or C 6 -C 6 alkylcarbonyloxy; a phenoxy group.

Of these, compounds of the formula I are particularly preferred, in which R @ ² and R @ ^{3 are} each independently hydrogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl. C 6 -C 6 alkyl, C 2 -C 15 alkylcarbonyl, C 2 -C 15 alkenylcarbonyl or C 4 -C 9 cycloalkylcarbonyl, which may be substituted by halogen, cyano, nitro or hydroxy, or R ² and R ^{3 is,} independently of one another, amino, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, phenylamino, C 2 -C 6 alkylcarbonylamino or C 2 -C 10 alkoxycarbonylamino.

In other groups of preferred compounds of formula (I)

I

X represents an oxygen atom, or

R ⁴ represents a phenyl group or a phenyl group which is substituted with halogen.

Preferred compounds of formula I are those in which:

R ^x is C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkylalkyl and C 1 -C 6 alkyl, C 1 -C 8 alkylcycloalkyl C 3 -C 8 alkyl, C 2 -C 10 alkenyl, C 3 -C 8 cycloalkyl and C 2 -C 6 alkenyl, C 2 -C 8 alkenylcycloalkyl C 3 -C 8 alkenyl and C 3 -C 8 alkynyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkylalkynyl and C 2 -C 6 alkynyl, C 2 -C 6 alkynylcycloalkyl 8 carbon atoms in the alkynyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, cycloalkenyls (C až-C 8) group, (C až-C až) cycloalkenylalkyl (C až-C až) alkyl group, (C až-C alkyl) alkylcycloalkenyl (C až-C až) group, cycloalkenylalkenyl having 5 to 8 carbon atoms in the cycloalkenyl moiety and 2 to 6 carbon atoms in the alkenyl moiety, alkenyl45 cycloalkenyl having 2 to 8 carbon atoms in the alkenyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylalkinyl having 5 to 8 carbon atoms C 2 -C 6 cycloalkenyl, C 2 -C 8 alkynylcycloalkenyl, C 5 -C 8 cycloalkenyl, C 3 -C 8 cycloalkylcycloalkyl, Cycloalkenyl, with 5 to 8 carbon atoms in each C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkyl and C 5 -C 8 cycloalkenyl, C 5 -C 8 cycloalkenylcycloalkyl and C 3 -C 8 cycloalkyl; C 2 -C 8 alkynyl and C 2 -C 6 alkenyl or C 2 -C 8 alkenyl-C 2 -C 6 alkynyl, which groups may be unsubstituted or substituted by halogen , cyano, nitro, oxo, -OR ^S , -S (O) JR ^e , -COOR ⁷ , -CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ^{X 2} , phenyl, biphenyl, naphthyl or heterocyclyl the phenyl, naphthyl and heterocyclyl substituents may be substituted with halogen, cyano, nitro, Kupino -0R ^a, -NR a R ^{XO XX} or CONR ^a R ^9, or

R ^x is heterocyclyl wherein the heterocycle is bonded to the thiatriazine ring via one of its carbon atoms and which heterocycle may be substituted by halogen, cyano, nitro, oxo, -0R ^a group -S (0) R ^e, -COOR ⁷ ,

XX

-CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ^xa , = N-NR ^{X 3} R ^X4 , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, phenyl, biphenyl, naphthyl, C 1 -C 8 alkyl substituted with halogen, cyano, nitro, -OR ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, alkenyl of 2 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, alkynyl, group having 2 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^a, CONR ^e R ⁹ or -NR ^XX R ^XO, cycloalkyl having 3 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^s , - CONR ^a R ⁹ or -NR ^XX R ^XO, cycloalkenyl of 5-8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, phenyl which is substituted with halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, -OR ³ , -CONR ^and R ⁹ or -NR ^XO R ^XX , biphenyl substituted with halogen , cyano, nitro, -0R ^a, -CONR ^a R® or -NR R ^{XO XX} or naphthyl which is substituted by halogen, cyano, nitro, -OR ^3, -CONR ^a R ^9, and -NR R ^{XO XX} or

R ^x is phenyl, biphenyl, naphthyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylbiphenyl, C 1 -C 4 alkylnaphthyl, alkenylphenyl C 2 -C 4 alkenyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkynyl, C 2 -C 4 alkynyl C 2 -C 4 alkynyl or C 2 -C 4 alkynyl-naphthyl which may be substituted by halogen, cyano, nitro, -OR ^S , -S (O) R ®, n

-COOR ^7, -CONR ^e R ⁹ or -NR ¹ R ^{1 O L} wherein

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 4 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms or an alkynyl group having 3 to 4 carbon atoms, n being 0, 1 or 2

R 8 represents a hydrogen atom or a cyano group when n is 0, or

R @ 1 represents C1 -C4 alkyl, C1 -C4 haloalkyl, phenyl, C1 -C4 alkylphenyl, halogenphenyl, heterocyclyl, halogenheterocyclyl or cycloalkyl; up to 6 carbon atoms,

R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, each of R ^a and R ^{3 is} independently hydrogen, phenyl, halo phenyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl; , a (C až-C alk) alkenyl group, a (C až-C alk) alkynyl group or a (C až-C alko) alkoxyalkyl group, or R® and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may: be halogenated; R ¹⁰ and R ¹¹ independently of one another are hydrogen, phenyl, halophenacyl C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 1 -C 4 alkynyl C 2 -C 4, formyl, C 1 -C 4 alkylcarbonyl or phenylcarbonyl, the phenyl radical of which may be substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, hydroxy , cyano, nitro or (C 1 -C 4) alkoxycarbonyl, or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated, and

R ^{X 2} is H, alkyl of 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms, phenyl, halophenyl, cyanophenyl, nitrophenyl, alkylphenyl, C 1 -C 4 alkyl, alkoxyphenyl C 1 -C 4 alkoxy or C 1 -C 4 phenylalkyl.

Particularly preferred of these compounds are those in which the alkyl group contains 1 to 10 carbon atoms, the cycloalkyl group containing 3 to 8 carbon atoms, the cycloalkylalkyl group having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl moiety. , (C 1 -C 8) alkylcycloalkyl, (C 3 -C 8) cycloalkyl, (C 2 -C 10) alkenyl, (C 3 -C 8) cycloalkyl, (C 2 -C 6) alkenyl; alkenylcycloalkyl having 2 to 8 carbon atoms in the alkenyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, alkynyl carbon atoms, cycloalkylalkynyl carbon atoms in the cycloalkyl moiety and 2 to 6 carbon atoms in the alkynyl moiety, alkynylcycloalkyl C 3 -C 8 alkynyl in the cycloalkyl moiety, a cycloalkenyl group of 5 to 8 carbon atoms, a cycloalkenylalkyl group of 5 to 8 carbon atoms of a 2 to 10 ring of a 3-8 group in the cycloalkenyl moiety and 1 to 6 carbon atoms of an alkyl moiety, an alkylcycloalkenyl group of 1 to 8 C 5 -C 8 alkyl, C 5 -C 8 cycloalkenyl alkenyl, C 2 -C 6 alkenyl, C 2 -C 8 alkenyl cycloalkenyl and C 5 -C 8 alkenylcycloalkenyl (C-C cyk) cycloalkenyl, (C až-Clal cyk) cycloalkenylalkynyl, (C až-C až 2) alkynyl, (C až-C 8) alkynylcycloalkenyl, (C až-C cyk až) cycloalkenyl), cycloalkylcycloalkyl having 3 to 8 carbon atoms in each cycloalkyl moiety , cycloalkenylcycloalkenyl of 5 to 8 carbon atoms in each cycloalkenyl moiety, cycloalkylcycloalkenyl of 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylcycloalkyl of 5 to 8 carbon atoms in the cycloalkenyl moiety, (C-C cyk) cycloalkyl, (Ciny-C alk alk) alkynylalkenyl, (C až-C až alk) or (C až až-Ceny alk) alkenylalkynyl (C až-C alk) alkynyl group, wherein: which groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo, -OR® group, -COOR ^7, -C0NR ^and R ^9, -NR ^XX R ^XO or phenyl, wherein the phenyl ring is unsubstituted or substituted by halogen, or

R ^x is heterocyclyl wherein the heterocycle is bonded to the thiatriazine ring via one of its carbon atoms and which heterocycle may be substituted by halogen, cyano, oxo, -0R ^the group -S (O) ^ R ^6, -COOR ⁷ , -CONR ^and R ®, -NR ^XO R ^XX , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl, cycloalkenyl C 5 -C 8 -alkyl, phenyl, C 1 -C 8 -alkyl substituted by halogen, cyano, -OR ^S , -CONR ^and R ⁹ or -NR ^XO R ^XX , C 2 -C 8 alkenyl alkyl which is substituted by halogen, cyano, -OR ^5, -CONR R® ^s or NR R ^{XO XX,} alkynyl group having 2 to 8 carbon atoms which is substituted by halogen, cyano, -0R ^a, -CONR ^and Or -NR ⁹ R ^XO R ^XX, cycloalkyl having 3 to 8 carbon atoms, which is substituted by halogen, cyano, -OR ^5, -CONR ^e R ⁹ or -NR ^XX R ^XO, cycloalkenyl of 5-8 carbon atoms which is substituted with halogen, cyano, -OR ⁵ , -CONR ⁵ R ⁹ or -NR ^XO R ^XX, or phenyl substituted with halogen, cyano, nitro, C 1 -C 4 alkyl, haloalkyl 1 to 6 carbon atoms, -OR ^5, -CONR ^e R ⁹ or -NR R ^{XO XX,} or

R ^x is phenyl, biphenyl, naphthyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylbiphenyl, C 1 -C 4 alkylnaphthyl, alkenylphenyl C 2 -C 4 alkenyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 alkynyl C 1-4 alkynyl or C 2-4 alkynyl-naphthyl which may be unsubstituted or substituted by halogen, cyano, -OR ³ , -S (O) _n R ^e , -COOR ⁷ , -CONR ^e R ⁹ or -NR ¹⁰ R ¹¹ , wherein

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenylalkyl having 1 to 4 carbon atoms C1-4 alkylcarbonyl, benzoyl, halobenzoyl, trialkylsilyl of 3-6 carbon atoms, cycloalkyl of 3-6 carbon atoms, alkenyl of 2-4 carbon atoms or alkynyl of 3 carbon atoms up to 4 carbon atoms, n is 0, 1 or 2,

R ^e represents a hydrogen atom or a cyano group when n is 0, or

R ^e is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl or C 1 -C 4 alkylphenyl,

R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, R ⁸ and R ⁹ are each independently hydrogen, phenyl, halophenyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl; , (C 3 -C 4) alkenyl, (C 4 -C 4) alkynyl or (C 2 -C 4) alkoxyalkyl, or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may: be halogenated, R ^x0 and R ^xx are each independently hydrogen, phenyl, halophenes a C1-4 alkyl group, a C1-4 haloalkyl group, a C1-4 cyanoalkyl group, a C3-4 alkenyl group, a C3-4 alkynyl group, an alkoxyalkyl group (C 2 -C 4), formyl, (C 1 -C 4) alkylcarbonyl or phenylcarbonyl, the phenyl radical of which may be substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, hydroxy, cyano, nitro or (C 1 -C 4) alkoxycarbonyl, or R ^xo and R ^xx together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated.

Particularly preferred of these compounds are those in which

R ^x is C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl C 1 -C 8 cycloalkyl and C 1 -C 6 alkyl, C 1 -C 8 alkylcycloalkyl C 3 -C 8 alkyl, C 2 -C 10 alkenyl, C 3 -C 8 cycloalkyl and C 2 -C 6 alkenyl, C 2 -C 8 alkenylcycloalkyl C 3 -C 8 alkenyl and C 3 -C 8 alkynyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkylalkynyl and C 2 -C 6 alkynyl, C 2 alkynylcycloalkyl up to 8 carbon atoms in the alkynyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, cycloalkenyl C 5 -C 8 cycloalkenylalkyl having 5 to 8 carbon atoms in the cycloalkenyl moiety and 1 to 6 carbon atoms in the alkyl moiety, alkylcycloalkenyl having 1 to 8 carbon atoms in the alkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety a (C 5 -C 8) cycloalkenylalkenyl group having 2 to 6 carbon atoms in the alkenyl moiety, an C 2 -C 8 alkenylcycloalkenyl group having 5 to 8 carbon atoms in the cycloalkenyl moiety, a C 5 -C 8 cycloalkenylalkinyl group cycloalkenyl and 2-6 carbon atoms in the alkynyl moiety, alkynylcycloalkenyl having 2 to 8 carbon atoms in the alkynyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkylcycloalkyl having 3 to 8 carbon atoms in each cycloalkyl alkenyl moiety, a group having from 5 to 8 carbon atoms in each give a cycloalkenyl moiety, a cycloalkylcycloalkenyl group having 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, a cycloalkenylcycloalkyl group having 5 to 8 carbon atoms in the cycloalkenyl moiety and 3 to 8 carbon atoms in the cycloalkylalkyl moiety up to 8 carbon atoms in the alkynyl moiety and 2 to 6 carbon atoms in the alkenyl moiety or an alkenylalkynyl group having 2 to 8 carbon atoms in the alkenyl moiety and 2 to 6 carbon atoms in the alkynyl moiety, which groups may be unsubstituted or halogen substituted, cyano, nitro, oxo, -0R ^the group, -COOR ^7, -CONR ^p R ^9, -NR ^XX R ^{1 O} or phenyl, wherein the phenyl ring is unsubstituted or substituted by halogen, or

R ^x represents a heterocyclyl group, the heterocycle being attached to the thiatriazine ring through one of its carbon atoms and wherein the heterocycle may be substituted by halogen, cyano, oxo, C 1 -C 4 alkoxy, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, C 1 -C 8 alkyl substituted with halogen, C 2 -C 8 alkenyl substituted with halogen, alkynyl (C 2 -C 8) group substituted by halogen or phenyl substituted by halogen, cyano, nitro, (C 1 -C 4) alkyl or (C 1 -C 4) alkoxy; or

R ^x represents phenyl, biphenyl, naphthyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylbiphenyl, C 1 -C 4 alkylnaphthyl, alkenylphenyl of 2 to 4 carbon atoms in the alkenyl part or alkynylphenyl having 2 to 4 carbon atoms in the alkynyl part, which groups may be unsubstituted or substituted by halogen, cyano, -0R ^p, s (O) _n R ^6, -COOR ⁷ , -CONR ^and R ⁹ or -NR ¹⁰ R ^{11: L} , wherein

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenylalkyl having 1 to 4 carbon atoms C1-4 alkylcarbonyl, benzoyl, halobenzoyl, trialkylsilyl of 3-6 carbon atoms, cycloalkyl of 3-6 carbon atoms, alkenyl of 2-4 carbon atoms or alkynyl of 3 carbon atoms up to 4 carbon atoms, n is 0, 1 or 2,

R ^e represents a hydrogen atom or a cyano group when n is 0, or

R ^e is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl or C 1 -C 4 alkylphenyl,

R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, R® and R ⁹ each independently represent a hydrogen atom, a phenyl group, a halogenophenyl group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyanoalkyl group having 1 to 4 carbon atoms , a (C až-C alk) alkenyl group, a (C až-C alk) alkynyl group or a (C až-C alko) alkoxyalkyl group, or R® and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may: be halogenated, R ^x0 and R ^xx are each independently hydrogen, phenyl, halophenes a C1-4 alkyl group, a C1-4 haloalkyl group, a C1-4 cyanoalkyl group, a C3-4 alkenyl group, a C3-4 alkynyl group, an alkoxyalkyl group C 2 -C 4, formyl, C 1 -C 4 alkylcarbonyl or phenylcarbonyl, wherein the phenyl radical in these groups may be unsubstituted or substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy carbon, hydroxy, cyano, nitro or (C 1 -C 4) alkoxycarbonyl, or R ^xo and R ^xx together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated.

Further preferred compounds of formula I are those in which the symbols R ² and R ³ independently of one another are hydrogen, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 6 carbon atoms which is substituted by halogen, cyano, , nitro, C 1 -C 4 alkoxy, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium, carboxyl, -COOM, where M is an ammonium or alkali or alkaline earth metal atom, or a C 3 -C 8 cycloalkyl group, a C 1 -C 5 alkylcarbonyloxy group, a phenylcarbonyloxy group, a naphthylcarbonyloxy group, a C 1 -C 6 alkylamino group, a C 1 -C 5 alkoxycarbonyl group , a 2-6-dialkylamino group like alkyl or phenyl, wherein the phenyl ring is unsubstituted or substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{1 O X 1,} an alkyl group having 1 to 4 carbon atoms, a formyl group, an alkylcarbonyl group having 1 to 4 carbon alkyl, COOR ⁷ alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms or ^a group CONR R®, or the radicals R ² and R ³ independently of one another are alkenyl with 2 to 6 carbon atoms, alkenyl (C 2 -C 6) -substituted by halogen, cyano, nitro, (C 1 -C 4) alkoxy, (C 3 -C 6) trialkylsilyl, hydroxy, amino, ammonium, (C 1 -C 4) trialkylammonium each alkyl moiety, a carboxyl group, a -COOM group, wherein M represents an ammonium group or an alkali atom or a C 1 -C 6 alkylamino, C 2 -C 5 alkoxycarbonyl, C 2 -C 6 dialkylamino or phenyl group, wherein the phenyl ring may be unsubstituted or substituted by halogen, cyano, nitro, -0R ^a, -NR ^XX R ^XO, alkyl having 1 to 4 carbon atoms, a formyl group, an alkylcarbonyl group having 1 to 4 carbon atoms, -COOR ^7, alkylthio having 1 to 4 carbon atoms, alkylsulfonyl of 1 up to 4 carbon atoms or CONR ® R ®, or R ² and R ³ independently represent C 3 -C 6 alkynyl, C 3 -C 6 alkynyl which is substituted by halogen, cyano, nitro, (C 1 -C 8) alkoxy, (C 3 -C 6) trialkylsilyl, hydroxy, amino, amine an ammonium group, a trialkylammonium group having 1 to 4 carbon atoms in each alkyl moiety, a carboxyl group, a -COOM group wherein M is an ammonium or alkali metal or alkaline earth metal atom, or an alkylamino group having 1 to 6 carbon atoms, an alkoxycarbonyl group having C 2 -C 5, C 2 -C 6 dialkylamino or phenyl, wherein the phenyl ring may be unsubstituted or substituted by halogen, cyano, nitro, -OR ®, -NR ^XO R ^XX , C 1 -C 4 alkyl , formyl, C 1 -C 4 alkylcarbonyl, COOR ⁷ , C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or CONR ® R ³ , or R ^a and R ³ independently of one another each represents a formyl group, an alkylcarbonyl group having 1 to 8 carbon atoms, an alkenylcarbonyl group (C až-C u) alkyl, (C až-C cyk) cycloalkylcarbonyl, (C až-C 9) cycloalkenylcarbonyl or (C až-C 8) cycloalkyl and (C až-C až) alkyl group; they may be unsubstituted or substituted by halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 alkylamino, C 2 -C 7 dialkylamino, carboxyl, -COOM, where M is an ammonium or alkali metal atom or an alkali earth metal or C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 1 -C 8 alkylaminocarbonyl or C 2 -C 8 dialkylaminocarbonyl group, or R ² and R ³ independently of one another are each heterocyclylo heterocyclylcarbonyl, heterocyclyl substituted with halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylcarbonyl, C 1 -C 5 alkylcarbonyl , C1 -C6 alkoxycarbonyl, aminocarbonyl, C1 -C6 alkylaminocarbonyl or C2 -C8 dialkylaminocarbonyl, or a heterocyclylcarbonyl group which is substituted by halogen, cyano, nitro, C1 -C4 -alkyl; C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, aminocarbonyl, C 1 -C 6 alkylamino or C 1 -C 5 alkylcarbonyloxy, or symbil R @ ² and R @ ³ independently represent phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenylalkylcarbonyl having 1 to 6 carbon atoms in the alkyl moiety, biphenylcarbonyl having 1 to 6 carbon atoms in the alkyl moiety, naphthylalkylcarbonyl; C 2 -C 6 alkyl, C 2 -C 6 phenylalkenylcarbonyl, C 2 -C 6 biphenylalkenylcarbonyl or C 2 -C 6 naphthyl alkenylcarbonyl, which may be unsubstituted or unsubstituted (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylthio, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkylcarbonyl, halogen, cyano, amino, nitro , skupi -OR ⁷ , C 1 -C 5 alkoxycarbonyl, hydroxy, C 1 -C 4 alkylsulfonyl, C 1 -C 5 alkylaminocarbonyl or C 2 -C 6 dialkylaminocarbonyl, or R ² and R ³ each independently represents a phenyl, naphthyl or heterocyclyl group, which groups may be unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio carbon atoms, carboxyl, -CONH4, C1 -C5 alkylaminocarbonyl, C2 -C7 dialkylaminocarbonyl, C1 -C4 alkylcarbonyl or C1 -C6 alkoxycarbonyl, or R @ ² and R @ ³ together with the nitrogen to which they are binding the Form a heterocyclic ring which may be substituted by C 1 -C 4 alkyl, C 1 -C 4 alkyl, halogen, cyano or nitro, or the radicals R ² and R ³ independently of one another are amino, C 1 -C (C 4 -C 6), (C 2 -C 6) dialkylamino, phenylamino, (C 1 -C 5) alkylcarbonylamino, (C 1 -C 5) alkoxycarbonylamino, hydroxy, (C 1 -C 4) alkoxy, (C 1 -C 5) alkylcarbonyloxy,

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 4 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino C 3 -C 6 trialkylsilyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl,

R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, R ^s and R ⁹ are each independently hydrogen, phenyl, halo-phenyl, (C až-C alky) alkyl, (C až-C hal) haloalkyl, (C až-C ky) cyanoalkyl; , a (C až-C alkeny) alkenyl group, a (C 4-C alk alk) alkynyl group or a (C atóm ktorý alebo) alkoxyalkyl group, or R ^môže and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may: be halogenated, R ^x0 and R ^xx are each independently hydrogen, phenyl, halophenes a C1-4 alkyl group, a C1-4 haloalkyl group, a C1-4 cyanoalkyl group, a C3-4 alkenyl group, a C3-4 alkynyl group, an alkoxyalkyl group C 2 -C 4, formyl, C 1 -C 4 alkylcarbonyl or phenylcarbonyl, the phenyl radical of which may be substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, hydroxy , cyano, nitro or C 1 -C 4 alkoxycarbonyl, or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated.

Among these compounds, particularly preferred are those in which R @ ² and R @ ³ each independently represent a hydrogen atom, a C1 -C6 alkyl group, a C1 -C6 alkyl group which is substituted by a halogen, a hydroxy group, amino, ammonium, C 1 -C 4 trialkylammonium, carboxyl, -COOM, where M is an ammonium or alkali metal or alkaline earth metal atom, or a C 1 -C 5 alkylcarbonyloxy group, phenylcarbonyloxy , (C 1 -C 6) alkylamino, (C 1 -C 5) alkoxycarbonyl or (C 2 -C 6) dialkylamino, or R ² and R ^{3 are} each independently formyl, C 1 -C 8 alkylcarbonyl, alkenylcarbonyl having 2 to 8 carbon atoms, cycloalk C 4 -C 9 -ylcarbonyl, C 6 -C 9 cycloalkenylcarbonyl or C 3 -C 8 cycloalkylalkylcarbonyl and C 1 -C 6 alkyl which may be unsubstituted or substituted by halogen, cyano , hydroxy, amino, carboxy, a group -COOM, wherein M is ammonium or an alkali metal or an alkaline earth metal, or the radicals R ² and R ³ independently of one another are heterocyclyl, heterocyclylcarbonyl, heterocyclyl which is substituted with halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy or C 1 -C 6 alkoxycarbonyl, or heterocyclylcarbonyl substituted with halogen, cyano, nitro, alkyl ovou 1 -C 4 alkyl, C 1 -C 4 alkyl or alkylcarbonyl having 1 to 4 carbon atoms, or the radicals R ² and R ³ independently of one another are phenylcarbonyl, bifenylkarbonylovú group, naphthylcarbonyl, fenylalkylkarbonylovú having (C 1 -C 6) alkyl, (C 1 -C 6) biphenylcarbonyl, (C 1 -C 6) naphthylalkylcarbonyl, (C 2 -C 6) phenylalkenylcarbonyl, (C 2 -C 6) biphenylalkenylcarbonyl C 6 -C 6 alkenyl or C 2 -C 6 naphthylalkenylcarbonyl, which groups may be unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio carbon, haloalkyl for (C 1 -C 4), (C 1 -C 4) alkylcarbonyl, halogen, cyano, amino, nitro, carboxyl, (C 1 -C 5) alkoxycarbonyl, hydroxy or (C 1 -C 4) alkylsulfonyl, or R ² and R ^{3 are} each independently phenyl, naphthyl or heterocyclyl, which may be unsubstituted or substituted by halogen, cyano, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylthio, carboxyl, (C 1 -C 5) alkoxycarbonyl, or R ² and R ³ together with the nitrogen atom to which they are attached form a heterocyclic ring which may be substituted with a C 1 -C 4 alkyl group C 4 -C 4 alkoxy, C 1 -C 4 alkoxy, halogen m or cyano.

Preferred compounds of formula I are especially those in which the symbols R ² and R ³ are each a hydrogen atom, or the symbols R ² and R ³ independently of one another are formyl, alkylcarbonyl having 1 to 8 carbon atoms, an alkenylcarbonyl group, C 2 -C 8, C 4 -C 9 cycloalkylcarbonyl, C 6 -C 9 cycloalkenylcarbonyl, or C 3 -C 8 cycloalkylalkylcarbonyl, and C 1 -C 6 alkyl, which may be be unsubstituted or substituted by halogen, cyano, hydroxy or amino, or the radicals R ² and R ³ independently of one another are phenylcarbonyl, where the phenyl ring is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkylthio with p C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyl, halogen, cyano, nitro, carboxyl, C 1 -C 5 alkoxycarbonyl, hydroxy or C 1 -C 4 alkylsulfonyl.

Other preferred compounds of formula I are those in which:

X is O or S (O) _x , wherein x is 0, 1 or 2, and

R ⁴ represents a methyl group which is substituted by halogen, cyano, nitro or OR ⁵ , or

R ⁴ is C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, cycloalkylalkyl (C 3 -C 8) cycloalkyl and (C 1 -C 4) alkyl or (C 1 -C 4) alkyl (C 3 -C 8) cycloalkyl group, which groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo or -OR ⁵ , or

R ⁴ represents a phenyl group which is substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloalkyl (C 1 -C 4), (C 1 -C 4) haloalkoxy, (C 1 -C 4) haloalkylthio, (C 2 -C 6) alkoxycarbonylalkoxy (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) alkyloxy group (C 1 -C 6) alkyl, (C 1 -C 6) alkylcarbonyl, -CONH ₂ , formyl, (C 1 -C 5) alkylaminocarbonyl, (C 2 -C 7) dialkylaminocarbonyl, (C 1 -C 4) alkylamino group, (C 2 -C 6) dialkylamino, trialkylsilylo (C 3 -C 6) alkyl, (C 1 -C 6) alkylcarbonylamino, (C 1 -C 6) alkylcarbonyloxy, phenoxy, halophenoxy or pyridyloxy group; or

R ⁴ is biphenyl, naphthyl, heterocyclyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylnaphthyl, C 1 -C 4 phenylalkyl or naphthylalkyl C 1 -C 4 alkyl, which groups may be unsubstituted or substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio (C 1 -C 4), (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 1 -C 4) haloalkylthio, (C 2 -C 6) alkoxycarbonylalkoxy (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfinyl; 1-4 carbon atoms, alk (C 1 -C 6) yloxycarbonyl, (C 1 -C 6) alkylcarbonyl, -CONH ₂ , formyl, C 1 -C 5 alkylaminocarbonyl, C 2 -C 7 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl carbon atoms, (C1-C6) alkylcarbonylamino, (C1-C6) alkylcarbonyloxy, phenoxy, halophenoxy or pyridyloxy, and

R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 4 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino C 3 -C 6 trialkylsilyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl.

Of these compounds, those in which

X represents an oxygen atom or a sulfur atom, and

R ⁴ represents a methyl group which is substituted by a halogen or a cyano group, or

R ⁴ is C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, cycloalkylalkyl C 3 -C 8 cycloalkyl and C 1 -C 4 alkyl or C 1 -C 4 alkylcycloalkyl C 3 -C 8 cycloalkyl, which groups may be unsubstituted or substituted by halogen, or cyano, or

R ⁴ is phenyl which is substituted by halogen, cyano, nitro, amino, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl , (C 1 -C 4) haloalkoxy, (C 2 -C 6) alkoxycarbonylalkoxy, (C 1 -C 4) alkylsulfonyl, (C 1 -C 6) alkyloxycarbonyl, (C 1 -C 6) alkylcarbonyl, formyl, (C 1 -C 6) alkyl group (C 4 -C 6), (C 2 -C 6) dialkylamino, (C 3 -C 6) trialkylsilyl or (C 2 -C 6) alkylcarbonyloxy, or

R ⁴ is biphenyl, naphthyl, heterocyclyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylnaphthyl, C 1 -C 4 phenylalkyl or naphthylalkyl C 1-4 alkyl, which may be unsubstituted or substituted by halogen, cyano, nitro, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 2 -C 6 alkoxycarbonylalkoxy, C 1 -C 4 alkylsulfonyl, C 1 -C 6 alkyloxycarbonyl, C 1 -C 6 alkylcarbonyl C 6 -C 3 trialkylsilyl Or C 1 -C 6 alkylcarbonyloxy.

Particularly preferred compounds of formula I are those in which

X represents an oxygen atom, and

R ⁴ is phenyl which is substituted by halogen, cyano, nitro, amino, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl , halogenomethoxy, (C 1 -C 4) alkylsulfonyl, (C 1 -C 6) alkyloxycarbonyl, (C 1 -C 4) alkylamino or (C 2 -C 6) dialkylamino.

Compounds of formula (I) may be prepared for:

On the one hand, by methods generally known using known starting materials, on the other i

using a method that was not generally known. In the latter way, which was not generally! known, starting from trihalogenated thiatriazine of formula II

Hal ·

(II) wherein the substituents Hal independently represent a fluorine, bromine or especially chlorine atom, the thiatriazine together with its preparation is described in Chem. Ber. (1991) 124, 1347-1352 and Z. Chem. 16 (1976) 358-359, and this compound of formula II is reacted with the corresponding organometallic compound of formula III to introduce the substituent R ¹

R ¹ -M (III) wherein R ^{1 is} as defined above and M represents a monovalent or polyvalent metal atom which, depending on the valence, may carry the corresponding number of R ¹ groups. Examples of suitable metals include, but are not limited to, lithium, magnesium, zinc, aluminum, silicon, and tin, as well as manganese and titanium. The polyvalent metal atoms may also carry, in addition to one or more R ^x groups, other substituents such as halogen, cyano, C 1 -C 4 alkyl or tetrafluoroborate. The organometallic compound of formula III can further be used in combination with salts such as aluminum chloride, tin chloride, zinc chloride or cerium chloride or aluminum bromide, zinc bromide and / or copper bromide, of which zinc chloride and zinc bromide are preferred.

Compounds of formula III may be prepared by conventional methods, for example by reacting the corresponding R ¹ -halogen halide with a metal M, if appropriate with the addition of a metal halide, or by halogen / metal exchange of R ^x -Br or

R ^x -I with a reactive organometallic compound, for example butyllithium, and reaction with a metal compound M carrying at least one leaving group such as halogen, or by proton abstraction of the R ¹ -H molecule with a strong base such as a metal alkoxide such as potassium tert-butoxide or a metal hydride such as sodium hydride or lithium aluminum hydride or a metal amide such as lithium diisopropylamide or, in particular, an organometallic compound such as butyl lithium and reacting with a metal compound M which carries at least one leaving group such as cyano, alkoxy or especially halo, optionally one or more alkyl groups having from 1 to 4 carbon atoms.

The introduction of the group R ^x may be carried out in an aprotic solvent such as a hydrocarbon, for example hexane, heptane or toluene, or an ether such as dioxane, diethyl ether or especially tetrahydrofuran, at temperatures from -100 ° C to 150 ° C, especially -80 ° C. C to 50 ° C (depending on solvent).

For compounds of formula IV in which the sulfur atom of tiatriazine is attached to the aromatic or heteroaromatic moiety R ^x , the reaction of the corresponding compound R ^x -H with the compound of formula II can be carried out under Friedel-Crafts conditions, i.e. in the presence of Lewis acid, aluminum chloride, zinc chloride or tin tetrachloride, in an aprotic solvent such as benzene, nitrobenzene or dichloromethane.

In the case of compounds of the formula I, in addition to the meanings given above, they represent a formula IX or X in which R ^x also represents a group

G *

E-O-C —οι 10B (IX) or

G

where

A represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a C 1 -C 7 alkyl group, a C 1 -C 7 alkyl group which is substituted by a halogen or a C 1 -C 3 alkoxy group or a C 1 -C 4 alkoxy group alkyl,

B represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a C 1 -C 7 alkyl group, a C 1 -C 7 alkyl group which is substituted by a halogen or a C 1 -C 3 alkoxy group or a C 1 -C 4 alkoxy group alkyl,

G represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen or alkoxy group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a trimethylsilyl group. hydrogen, fluorine, chlorine, bromine or iodine, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, thiocyanato, cyano or C 1 -C 5 alkylcarbonyloxy and 4-carbon C-carbon atoms or halogen, is C1-C8alkyl substituted by C1-C8alkoxy, C3-C8-benzyloxy, C3-C8-cycloalkyl, C1-C4-alkoxy, acetoxy, benzyloxy, alkyl, or halogen, C 1 -C 5, C 6 -C 8 aryl; with carbon atoms or (alkyl) _and silyl of 1 to 4 carbon atoms in each alkyl moiety, the compounds of formula (IV) may be prepared preferably from compounds of formula (XI)

G ^B - - / / (XI)

E-O ^A in which the substituents A and E, A and B, AaGaGaE can in each case always form a ring together, for example in the case of A and E

in the case of A and B

in the case of G and E

or

where

R c is C 1 -C 3 alkyl alkoxy benzyloxy or halogen, carbon atoms, acetoxy, and n is 0, 1, 2 or 3 by reacting a compound of formula XI with a compound of formula II in the presence or absence of a Lewis acid such as aluminum chloride, zinc chloride or tin tetrachloride in an aprotic solvent such as hexane, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, ether or tetrahydrofuran at temperatures from -78 ° C to boiling point and, if desired, the crude product obtained is subsequently reacted with an acid-binding agent such as a tertiary amine, for example triethylamine or pyridine, or a mineral base, for example sodium bicarbonate or potassium carbonate, optionally in aqueous solution, with the aim of not neutralization of H-halogen acid.

If the reactivity of the substituent ^R1 in the compound of formula I results in the preparation of organometallic compounds of formula III are difficult, then this labile functional group ^R1 can advantageously be protected and subsequently re-eliminated at the level of the compounds of the formulas IV, VI, VIII or I, , analogous to the procedure described, for example, in Protective Groups in Organic Synthesis, Th. W. Greene and PGM Wuts, Wiley Interscience, 1991. For example:

(a) the alcohol may be protected in the form of tert-butyldimethylsilyl ether and this protecting group may be removed with tetrabutylammonium fluoride; or

(b) the carbonyl group may be protected in the form of 1,3-dioxane and then hydrolyzed again under acidic conditions to form a carbonyl group; or

c) the carboxyl group can be protected in the form of an orthoester and then recovered under aqueous acidic conditions followed by basic conditions.

The reactive substituents in ^R1 in the compounds of formula I can also be introduced by known methods from less reactive precursors at the level of the compounds of the formulas IV, VI, VII or I, e.g., as described in Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Editor J. March, McGraw-Hill, 1983, or Comprehensive Organic Transformations, edited by RC Larock, VCH, 1989. Such less reactive precursors may be, for example, halogens such as bromine, chlorine or iodine, carbon-carbon double or triple bonds, or ethers and thioethers.

A wide variety of suitable conversion reactions for the preparation of functional groups are described in the literature. For example:

(a) the halide may be converted by reduction into the corresponding alkane or by nucleophilic substitution into the corresponding nitrile, ether, thioether, ester, azide or thiocyanate, or

(b) the carbon-carbon double bond may be hydrogenated, halogenated in the allyl position, oxidized to form the corresponding epoxide or cis-diol, or subjected to ozonolysis to form a carbonyl derivative or oxidative hydroboration to form an alkanol, or carboxylic acid, or

d) the thioether can be oxidized to form a sulfoxide or sulfone, the latter compounds being deprotonated in position and further reacted with electrophilic reagents; or

e) the azide can be reduced to give the corresponding amine and, if desired, subsequently acylated.

The resulting compounds of formula IV

Hai

they are new and thus also form part of the invention.

The substituents -NR ² R ³ and -XR * may then be introduced into the compound of formula IV in any desired order.

Reaction of compounds of formula IV with compounds of formula V

H-XR * (V) wherein X and R ^{4 are} as defined above to give compounds of formula VI

(VI) is preferably carried out in such a way that, prior to reaction with the compounds of formula IV, the compounds of formula V are preconditioned by reaction with a base such as a metal hydride such as lithium, sodium or potassium hydride, a metal hydroxide such as sodium , or a basic salt such as sodium carbonate or potassium carbonate, preferably in equivalent amounts. Alternatively, the above bases may also be added to the reaction mixture of compounds of formulas IV and V. Solvents suitable for this step are hydrocarbons such as hexane or toluene, halogenated hydrocarbons such as chlorobenzene, ethers such as tetrahydrofuran, dioxane or diethyl ether, and tertiary amides such as dimethylformamide. A mixture of these solvents with water may also be used, in which case it is preferable to use a phase transfer catalyst. Reaction temperatures are usually between -50 ° C and 100 ° C, preferably between 0 ° C and 40 ° C.

The compounds of formula (V) are known and can be prepared by a person skilled in the art.

The compounds of formula (VI) are novel and also form part of the invention.

They can be transformed into the final products of formula I by reaction with a compound of formula VII

M ^X -NR ² R ³ (VII) wherein R ² and R ³ are as defined above and M ^x represents a hydrogen or metal atom such as lithium, sodium, potassium or calcium, preferably in the presence of a base. If R ² and / or R ³ represents a hydrogen atom, then M ^x preferably represents a hydrogen atom. When R ² or R ³ is an acyl group, the M ^x preferably represents lithium, sodium or potassium.

Solvents suitable for this reaction are hydrocarbons such as hexane or toluene, halogenated hydrocarbons such as chlorobenzene or dichloromethane, ethers such as diethyl ether, dioxane or tetrahydrofuran, alcohols such as ethanol or isopropanol, esters such as ethyl acetate, nitriles such as acetonitrile, or water. Reaction temperatures range from -70 ° C to 100 ° C, in particular 0 ° C to 40 ° C.

When M ¹ represents a hydrogen atom, an acid binding agent is preferably used to capture the acid HHal. It may be, for example, a second equivalent of a compound of formula VII or a tertiary amine such as triethylamine, pyridine or an inorganic base such as sodium carbonate, potassium carbonate or sodium bicarbonate. Where R ² , R ³ and M ^x represent hydrogen atoms, an excess of the base may be used. This process can be carried out under pressure.

Compounds of formula (VII) and their preparation are described in the literature.

The reaction conditions to be observed in the case of the reaction of a compound of the formula VI with a compound of the formula VII should also be used when the compound of the formula IV is first reacted with a base of the formula VII. The resulting compounds of formula VIII

NR ² R ³

Hal are also novel and form part of the invention.

Further reactions of compounds of formula VIII with compounds of formula V are carried out analogously to the procedure for reaction of compounds of formulas IV and V. However, an amine such as triethylamine is added to the reaction mixture in amounts ranging from catalytic to excess.

The final products of formula (I) may be isolated by conventional concentration and / or evaporation of the solvent and purified by recrystallization or trituration of the solid residue with non-readily soluble solvents such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, or chromatographic procedures.

Other compounds of formula I can be prepared by conventional derivatization of compounds of formula I.

A variety of methods and techniques, such as the following, are suitable for use in the present invention of the compounds of Formula I, IV, VI or VIII or compositions comprising the compounds:

(i) Seed dressing

(a) The seeds shall be pickled with the active substance in the form of a wettable powder, by shaking in the container, until the active substance is evenly distributed on the seed surface (dry seed dressing). Up to 4 g of active compound of the formula I, IV, VI or VIII (in the case of 50% of the formulation up to 8.0 g of wettable powder) per kg of seed are used.

b) The seeds are pickled with an emulsion concentrate of the active ingredient or an aqueous solution of the active ingredient of the formula I, IV, VI or VIII formulated as a wettable powder by method a) (wet seed dressing).

c) The pickling is carried out by dipping the seeds into a mixture containing up to 1000 ppm of the active compound of the formula I, IV, VI or VIII for 1 to 72 hours and optionally drying the seeds (seed dipping).

Seed pickling or the treatment of seedlings which have just begun to germinate is a naturally advantageous method of application, since the application of the active substance is entirely aimed at the target culture. Usually 0.001 to 4.0 g of active substance per kg of seeds are used, and according to a method which also allows the addition of other active substances or microelement nutrients (repeated pickling), it may deviate upwards or downwards from the indicated limit concentrations.

(ii) Controlled release of the active substance

The active substance is applied in solution to mineral granular carriers or polymerized granules (urea / forataldehyde) and allowed to dry. If desired, a coating (coated granulate) may also be used to allow controlled release of the active ingredient over a period of time.

The compounds of formula (I), (IV), (VI) or (VIII) may be used as pure active compounds, i. as obtained by synthesis, however, preferably they are formulated in conventional manner with the carriers and excipients commonly used in the art of formulation, for example to form emulsion concentrates, direct spray solutions or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Application methods such as spraying, misting, dusting, soaking, scattering or potting as well as the nature of the composition are selected according to the desired results and prevailing conditions.

The formulations, i. compositions, preparations or combinations comprising an active ingredient of the formula I, IV, VI or VIII or at least one active ingredient of the formula I, IV, VI or VIII and, if desired, one or more solid or liquid additives are prepared by known means by means of thorough mixing and / or grinding of the active compounds with additives, for example solvents or solid carriers. In addition, surfactants can also be used to prepare formulations.

Suitable solvents are: aromatic hydrocarbons, in particular octagonal to twelve-carbon fractions, such as mixtures of alkylbenzenes, for example mixtures of xylenes or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols such as ethanol, propanol or butanol; glycols, as well as their ethers and esters, such as propylene glycol or dipropylene glycol ether; ketones such as cyclohexanone, isophorone or diacetone alcohol; strong polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or water; vegetable oils and esters thereof such as rapeseed oil, castor oil or soybean oil; and optionally also silicone oils.

Solid carriers which are used, for example, for dusts and dispersible powders are usually ground natural materials such as calcite, talc, kaolin, montmorillonite or attapulgite. High disperse silicon dioxide or high disperse absorbent polymers can also be added to improve physical properties. Suitable granular absorbent granule carriers are porous types of carrier materials, for example pumice, brick, sepiolite or bentonite, and suitable non-absorbent carrier materials are, for example, calcite or sand. In addition, a variety of pregranulated materials of an inorganic or organic nature, such as, in particular, dolomite or crushed plant residues, may be used.

Suitable surfactants are nonionic, cationic and / or anionic surfactants with good emulsifying, dispersing and wetting properties, depending on the nature of the active compound of the formula I to be formulated. It is understood that the term surfactants also encompass surfactant mixtures.

Suitable anionic surfactants can be either so-called &quot; water-soluble soaps or water-soluble synthetic surfactants.

Soaps may include alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids (containing up to 22 carbon atoms), for example sodium or potassium salts of oleic or stearic acid, or natural mixtures of fatty acids, which may be obtained for example, coconut or tallow oil. Fatty acid methyltaurinates should also be mentioned.

However, so-called synthetic surfactants are used more frequently, in particular fatty alcohol sulphonates, fatty alcohol sulphates, sulphonated benzimidazole derivatives or alkylarylsulphonates.

Fatty alcohol sulphonates or fatty alcohol sulphates are usually in the form of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts, and usually contain an alkyl radical of 8 to 22 carbon atoms, the alkyl also including the alkyl portion of the acyl radicals, for example, include the sodium or calcium salt of lignosulfonic acid, dodecylsulfuric acid esters, or a mixture of fatty alcohol sulfates made from natural fatty acids. This group also includes salts of sulfuric acid esters and sulfonic acids of fatty alcohol addition products with ethylene oxide. The sulfonated benzomidazole derivatives preferably contain two sulfonyl groups and a fatty acid moiety of about 8 to 22 carbon atoms. Examples of alkylarylsulfonates include, for example, sodium, calcium or triethanolamine salt and dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or the naphthalenesulfonic acid-formaldehyde condensation product.

Suitable phosphates, for example salts of phosphoric acid esters and p-nonylphenol adducts with 4-14 moles of ethylene oxide, or phospholipids are also suitable.

Suitable nonionic surfactants are, in particular, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which may contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon residue and 6 to 18 atoms alkylphenols.

Other suitable nonionic surfactants are the water-soluble addition products of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and an alkylpolypropylene glycol having from 1 to 10 carbon atoms in the alkyl chain containing from 20 to 250 ethylene glycol ether groups. The above compounds usually contain 1 to 5 units of ethylene glycol per propylene glycol unit.

Examples of nonionic surfactants include nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene and polyethylene oxide addition products, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxyethoxyethanol.

Other suitable substances are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are in particular quaternary ammonium salts which contain at least one alkyl radical of 87 to 22 carbon atoms as a nitrogen atom substituent and, as further substituents, lower, halogenated or non-halogenated, alkyl groups, benzyl groups or lower hydroxylalkyl groups. These salts are preferably in the form of halides, methyl sulfates or ethyl sulfates such as stearyltrimethylammonium chloride or benzyldi (2-chloroethyl) ethylammonium bromide.

Surfactants commonly used in formulations that can also be used in the compositions of the invention are described, inter alia, in the following publications:

Mc Cutcheon's Detergents and Emulsifiers Annual, Mc Publishing Corp., Glen Rock, New Jersey, 1988,

- M. and J. Ash, Encyclopedia of Surfactants, vol

I-III, Chemical Publishing Co., New York, 1980-1981,

Dr. Helmut Stache Tensid-Taschenbuch, Carl Hanser Verlag, Munich / Vienna 1981.

The herbicidal compositions usually contain from 0.1 to 99%, in particular from 0.1 to 95%, of active compound of the formula I, up to 99% of solid or liquid additives and from 0 to 25%, in particular from 0.1 to 25% of surfactant.

While concentrated compositions are preferable as commercial goods, the end consumer usually uses dilute compositions.

The compositions may also contain other additives, such as stabilizers, for example, non-oxidized or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), anti-foaming agents such as silicone oil, preservatives, viscosity control agents, binders, tackifiers such as fertilizers or other active substances to achieve special effects.

They have preferred compositions (the percentages are not particularly the following weight percentages):

Emulsifiable concentrates:

surfactant solvent up to 90%, preferably 5 to 50% to 30%, preferably 10 to 20% 15 to 94%, preferably 70 to 85%

dusts:

active substance solid carrier

0.1 to 50%, preferably 0.1 to 1% 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates:

active substance water surfactant

Wettable powders:

surfactant solid carrier up to 75 L, preferably 10 to 50% 94 to 24%, preferably 88 to 30% 1 to 40%, preferably 2 to 30%

0.5 to 90%, preferably 1 to 80% 0.5 to 20%, preferably 1 to 15% 5 to 95%, preferably 15 to 90%

Kibble:

active substance solid carrier

0.1 to 30%, preferably 0.1 to 15% 99.5 to 70%, preferably 97 to 85%

The active compounds of the formula I are usually used successfully in application rates of from 0.001 to 5 kg / ha, in particular from 0.005 to 2 kg / ha. The dose required to achieve the desired effect can be determined experimentally. It depends on the type of effect, the stage of development of the crop plant and weeds, as well as the individual application (site, time, procedure) and can vary widely due to these parameters.

The compounds of the formula I possess growth inhibitory and herbicidal properties which make them very suitable for use in crops of crops, in particular in cereals, cotton, soya, rape, maize and rice.

The following examples illustrate the invention in more detail, without limiting the scope thereof in any way.

The nomenclature below is based on the following numbering:

5 / ^{Ν Ν} Λ

N ^{== /} 2 ³

DETAILED DESCRIPTION OF THE INVENTION

Preparation examples

Example H1

Preparation of 3,5-dichloro-1-pentylthiatriazine

A solution of aluminum chloride (13.4 g, 0.1 mol) in tetrahydrofuran (400 ml) was cooled to -70 ° C. A solution of pentylmagnesium bromide in ether is then added dropwise, the mixture is allowed to warm to 20 ° C and after 15 minutes is cooled again to -70 ° C. Then 20.5 g of trichlorothiatriazine in 50 ml of tetrahydrofuran are added with stirring. The temperature of the reaction mixture is maintained at the above value for 2 hours. The reaction mixture was then allowed to warm to room temperature and poured into 400 L of ice water. The organic phase is treated with dilute aqueous hydrochloric acid, then washed with water to neutral pH and dried using sodium sulfate. After filtration and concentration of the phase, an oily residue is obtained which is taken up in 200 ml of hexane. The insoluble components were removed and the remaining solution was cooled. White crystals of the above compound are formed which, after recrystallization, have a melting point of 34 ° C.

Example H2

Preparation of 3,5-dichloro-1-methylthiatriazine

A solution of 18.5 g (0.09 mol) of trichlorothiatriazine in 200 ml of methylene chloride is cooled to -75 ° C. Dimethylaluminum chloride solution is then added dropwise under a protective gas atmosphere. the temperature should not exceed -65 ’C. The reaction mixture is then stored at -70 ° C for 40 minutes. The temperature is then allowed to rise to -45 ° C and 9 ml of water is added dropwise. The mixture was allowed to warm to room temperature, then filtered and the filtrate was dried using sodium sulfate. After concentration, a residue is obtained which is taken up in 50 ml of hexane and 20 ml of ether. The crude product was filtered off and then washed with hexane and dried in vacuo. Colorless crystals of the above compound are obtained, which melts with decomposition at 101 ° C.

Example H3

Preparation of 3- (2-ethoxycarbonylphenyloxy) -5-chloro-1-phenyltriazine

3.4 g of ethyl salicylate are dissolved in 15 ml of dimethylformamide and 0.88 g of sodium hydride (55% in oil) is added at 0-10 ° C. This solution was then added dropwise to a solution of 5.0 g of 3,5-dichloro-1-phenylthiatriazine (prepared analogously to Example H1) in 10 ml of dimethylformamide. The mixture is stirred for 12 hours at room temperature, then filtered and concentrated. The residue is taken up in methylene chloride, washed with water, dried over sodium sulphate and evaporated. After chromatography on silica gel using hexane / ethyl acetate (7: 1) as the eluent and recrystallization from the above mixture, crystals of the title compound of melting point 88-90 ° C are obtained.

Example H4

Preparation of 3-amino-5-chloro-1-methylthiatriazine

To a solution of 11.04 g of 3,5-dichloro-1-methylthiatriazine (obtained as described in Example H2) in 1.5 L of acetonitrile is introduced ammonia at 10-20 ° C. The mixture is stirred for 1.5 hours at 20 ° C and then 120 ml of water are added. The mixture is cooled to 5 ° C, the solid is filtered off, the residue is washed with water and cold acetonitrile and ether and dried.

The above product is obtained, which melts with decomposition at 156 ° C.

Example H5

Preparation of 3-chloro-5-isopropylamino-1-methylthiatriazine

To a solution of 23.0 g of dichloromethylthatriazine (obtained as described in Example H2) in 175 ml of tetrahydrofuran is added dropwise 14.8 g of isopropylamine at room temperature. Ethyl acetate and water were then added to the reaction mixture. The product is extracted with ethyl acetate, this phase is washed with water and dried over sodium sulfate. The mixture was filtered and the filtrate was concentrated, the crude product was then shaken with methylene chloride and the mixture was filtered again. Hexane was added to the filtrate, the mixture was stirred for 2 hours, filtered and the residue was washed with pentane and dried. The above compound is obtained in crystalline form, m.p. 120-122 ° C.

Example H6

Preparation of 3-amino-5- (2,6-dichlorophenoxy) -n-pentylthiatriazine

2.2 g of aminochloropentylthiatriazine (obtained by the methods described in Examples H1 and H4), 1.6 g of dichlorophenol, 0.4 g of sodium hydroxide (dissolved in 1 ml of water) and 1.48 g of a 40% aqueous trimethylamine solution are introduced into 100 ml. tetrahydrofuran. The mixture was stirred for 12 hours and concentrated and the residue was stirred with water and diethyl ether. After filtration, the solid is washed and dried. Recrystallization from tetrahydrofuran / hexane gave the title compound, which melted with decomposition at 200 ° C.

Example H7

Preparation of 3-methoxy-1-methyl-5-methyl-aminothiazine and triazine

To a suspension of 10.0 g of 3-chloro-1-methyl-5-methylaminothiatriazine (obtained in an analogous manner to that described in Example H4) in 250 ml of methanol cooled to 15 DEG C. was added 123 mmol of sodium methoxide and introduced. 2.6 g of trimethylamine. The mixture was stirred for 14 hours and then evaporated, the residue was stirred with methylene chloride, filtered and the solid was washed with pentane and dried. There was thus obtained the above compound with a melting point of 153-154 ° C.

Example H8

Preparation of 3,5-dichloro-1-phenylthiatriazine

To a solution of 10.2 g (0.05 mol) of trichlorothiatriazine and 7.5 g (0.05 mol) of phenyltrimethylsilane in 40 ml of dichloromethane at -20 ° C was added 0.15 g of aluminum chloride. The reaction mixture was slowly warmed to 20 ° C and stirred at this temperature for 2 hours. Then 300 g of ice-water are added and the mixture is extracted with dichloromethane. The combined organic phases are washed with water until neutral pH and dried over sodium sulfate. After filtering off the drying agent and concentrating the filtrate, the desired product is obtained in the form of crystals having a melting point of 91-94 ° C.

Example H9

Preparation of 1- (tert-butylethynyl) -3,5-dichlorothiatriazine

To a solution of 52.4 g (0.26 mol) of trichlorothiatriazine in 400 ml of dichloromethane at -75 ° C was added dropwise a solution of lithium tetrakis (tert-butylethynyl) alanate prepared from 3.24 g (0.0855 mol) lithium aluminum hydride, 0.2 g diethylamine and 33.7 g (0.41 mol) tert-butylacetylene in 250 ml tetrahydrofuran analogous to Bull. Acad. Sci. of USSR 1965, p. 165-167, edited by LI Zakharin et al. The temperature of the reaction mixture is maintained at the above value for 1 hour. A cold solution of 48 g of Rochelle salt and 9 g of potassium carbonate in 450 ml of water is added. After further addition of 1 L of water and 1 L of ether, the phases are separated. The aqueous phase is extracted with ether and the organic phase is washed with saturated sodium bicarbonate solution to neutral pH and dried over sodium sulfate. Removal of the desiccant by filtration and evaporation of the filtrate gave the desired product as crystals. Crystallization from hexane provides mp 73-74. ⁵ ° ^C ·

Example H10

Preparation of 3,5-dichloro-1-phenylthiatriazine

To a vigorously stirred suspension of 6.0 g (0.045 mol) of aluminum chloride in 80 ml of benzene and 10 ml of pentane at 0 ° C was slowly added dropwise a solution of 5.12 g (0.025 mol) of trichlorothiatriazine in 20 L of benzene. The reaction mixture is stirred for one hour at 0 ° C and then for another hour at 20 ° C. The reaction mixture is recooled to 0 ° C and ice and ether are added. The aqueous phase is extracted with ether and the combined organic phases are washed with an aqueous saturated sodium bicarbonate solution to neutral pH and dried over sodium sulfate. After removal of the desiccant by filtration and concentration of the filtrate, the crude product obtained is the title compound, which after chromatographic purification is identical to the compound obtained in Example H8.

Example Hli

Preparation of 3-amino-1-cyclohexyl-5-methanesulfinylthatriazine

To the vigorously stirred suspension 4.57 g (0.0187 mol)

Of 3-amino-1-cyclohexyl-5-methylthiotriazine in 70 ml of chloroform and 1.9 g of sodium bicarbonate is added dropwise over a period of 1.5 hours at 20 DEG C. to a solution of 6.45 g (0.02057 mol) of 3-chloroperbenzoic acid. of acid in 110 ml of chloroform. The reaction mixture is further stirred for 4 hours and then 180 ml of an aqueous half-saturated sodium bicarbonate solution are added. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over sodium sulfate. After removal of the desiccant by filtration and concentration of the filtrate, the residue is subjected to flash chromatography on silica gel, eluting with ethyl acetate / ethanol (4: 1). Recrystallization from ethyl acetate / methylene chloride gave the desired product as crystals which melted with decomposition at 134-138 ° C.

Example H12

Preparation of 1-cyclohexyl-3-isopropylthio-5-propylaminothiothriazine

To a solution of 1.75 g (0.006 mol) of 3-chloro-1-cyclohexyl-5-isopropylthiotriazine in 25 ml of tetrahydrofuran at 20 ° C was added dropwise 0.77 g (0.013 mol) of propylamine in 5 ml of tetrahydrofuran. After 1 hour, the reaction mixture is filtered under suction through a pad of silica gel and the residue is washed with tetrahydrofuran. The filtrate was evaporated and the residue was recrystallized from ethyl acetate / hexane. The desired compound is obtained in the form of crystals having a melting point of 73-74 ° C.

Example H13

Preparation of 3-amino-1- (3-bromo-2-methoxytetrahydropyran-3-yl) -5-chlorothiatriazine

To a suspension of 1.16 g (0.005 mol) of 3-amino-5-chloro-1- (5,6-dihydro-4H-pyran-3-yl) thiatriazine in 40 ml of methanol is added a solution of 0, 80 g (0.005 mol) of bromine in 10 ml of methanol are then stirred at 20 DEG C. for 1 hour. Subsequently, the reaction mixture is evaporated in vacuo, the residue is taken up in dichloromethane and the mixture is extracted by shaking with saturated sodium bicarbonate solution. The organic phase was separated and dried over sodium sulfate. After removal of the desiccant by filtration and concentration of the filtrate, the residue obtained is triturated with ether. The desired compound is obtained in the form of crystals which melt on decomposition at 188 ° C.

Example H14

Preparation of 3-amino-5-chloro-1- (2-methoxytetrahydropyran-3-yl) thiatriazine

A suspension of 0.61 g of 3-amino-1- (3-bromo-2-methoxytetrahydropyran-3-yl) -5-chlorothiatriazine, 0.06 g of bisazobutyronitrile and 0.62 g of tri-n-butyltin hydride in 50 ml of benzene is stirred at reflux temperature. After 1 hour the mixture was evaporated in vacuo and the residue was stirred with hexane. After filtration and washing of the crystals with hexane, the product is recrystallized from diisopropyl ether. The desired product melts at 167-168 ° C.

Example H15

Preparation of 3,5-dichloro-1- (2,3-dimethylpropyl) thiatriazine

To a mixture of 26.9 g (0.198 mol) of zinc chloride and 400 ml of tetrahydrofuran at -20 ° C was slowly added a Grignard solution prepared from 29.9 g (0.198 mol) of 1-bromo-2,2-dimethylpropane. The mixture is warmed to 0 ° C, then cooled again to -30 ° C and a solution of 40.5 g 1,3,5-trichlorothiatriazine in 200 ml tetrahydrofuran is added dropwise at this temperature. The temperature is slowly raised to 0 C C and maintained at 0 C.C for 2 hours. The reaction mixture was then poured into 600 g of an ice / water mixture and extracted with pentane. The organic phase is washed with aqueous sodium bicarbonate solution to neutral pH and then dried over sodium sulphate. After removal of the desiccant by filtration and concentration of the filtrate, the residue is recrystallized from pentane. Crystals of the desired product have a melting point of 48-51 ° C.

Example H16

Preparation of 2- (1-cyclohexyl-5-phenoxytiatriazin-3-yl) isoindole-1,3-dione

A mixture of 1.0 g (0.00344 mol) of 3-amino-1-cyclohexyl-5-phenoxytiatriazine, 0.69 ml (0.0086 mol) of pyridine and 0.55 ml (0.00378 mol) of phthalic acid dichloride in 30 ml. ml of 1,2-dimethoxyethane is stirred at reflux for 6 hours. After the mixture has cooled, it is poured into 70 ml of saturated aqueous sodium bicarbonate solution and the mixture is extracted with ethyl acetate, and the organic phase is dried over sodium sulphate. After filtration and concentration of the organic phase, the residue is subjected to flash chromatography on silica gel using ethyl acetate / hexane (35:65) as eluent. Recrystallization from ether / hexane gave the title compound as crystals, m.p. 145-146 ° C.

Example H17

Preparation of 3-methoxy-1-methyl-5-methylaminothiatriazine

To a suspension of 10.0 g (0.056 mol) of 3-chloro-1-methyl-5-methylaminothiothriazine in 250 ml of methanol at 15 ° C was added 2.6 g (0.045 mol) of trimethylamine. The reaction mixture was stirred for 14 hours and then evaporated in vacuo. Stir the residue with dichloromethane and filter through a pad of diatomaceous earth. The filtrate obtained is evaporated and the product is stirred with pentane and filtered under vacuum. Washing the solid obtained by filtration under vacuum with pentane and drying afforded the title compound as crystals, m.p. 153-154 ° C.

Example H18

Preparation of 3- (3-cyanopropylamino) -1-cyclohexyl-5-phenoxytiatriazine

To a solution of 2.98 g (0.00746 mol) of 3- (N-3-cyanopropylacetamido) -1-cyclohexyl-5-phenoxytiatriazine in 50 mL of ethanol was added

0.35 g (0.00875 mol) of sodium hydroxide. The reaction mixture is stirred for 0.5 hour at 22 ° C, then 400 ml of water are added and the suspension obtained is filtered under vacuum. The solid obtained by filtration under vacuum is washed with water and dried. The desired compound is obtained in the form of crystals having a melting point of 170-172 ° C.

Example H19

Preparation of 3- (N-3-cyanopropylacetamido) -1-cyclohexyl-5-phenoxytia triazine

To a solution of 2.5 g (0.00752 mol) of 3-acetamido-1-cyclohexyl-5-phenoxytiatriazine in 50 L of Ν, Ν-dimethylformamide at 40 ° C was added 0.22 g (0.00902 mol) of sodium hydride. After gas evolution had ceased, 4-bromopropionitrile (1.14 mg, 0.001128 mol) was added at 22 ° C and the mixture was stirred for 1 hour. Water was carefully added and then the reaction mixture was poured into 80 mL of water and the product was extracted with ethyl acetate. The organic phase is washed with brine and dried over sodium sulfate. After removal of the desiccant by filtration and concentration of the filtrate, the crude product is subjected to flash chromatography on silica gel using a 1: 1 mixture of ethyl acetate and hexane as eluent. Evaporation of the fractions yields the title compound as an oil.

Example H20

Preparation of 1-cyclohexyl-3-valeroylamino-5-phenoxytiatriazine

To a suspension of 1.0 g (0.00344 mol) of 3-amino-1-cyclohexyl-5-phenoxytiatriazine in 40 ml of 1,2-dichloroethane was added 0.92 g (0.00344 mol) of 2-valeroyl-3-oxo -4,5-benzo-1,2-thiazoline-1,1-dioxide, prepared analogously to that described in Syntethetic Communications 14 (4), 353-362 (1984), 0.72 ml (0.00516 mol) of triethylamine and a catalytic amount of 4-dimethylaminopyridine. The reaction mixture is stirred for 12 hours at reflux and then evaporated in vacuo. The residue is purified by chromatography on silica gel using toluene / ethyl acetate (4: 1). Recrystallization from ether / hexane gave the desired product as crystals, mp 116 ° C.

Example H21

Preparation of 3-acetamido-1-pentyl-5-phenylthiothatriazine

To a solution of 1.4 g (0.00475 mol) of 3-amino-1-pentyl-5-phenylthiothiothriazine in 50 ml of 1,2-dimethoxyethane was added 0.75 g (0.0095 mol) of pyridine and 0.97 g ( 0.0095 mol) of acetic anhydride and the reaction mixture is stirred for 12 hours at reflux. The reaction mixture was then evaporated in vacuo and ethyl acetate and water were added to the residue. The organic phase was separated, washed with water and dried over sodium sulfate. After removal of the desiccant by filtration, the filtrate is concentrated and the residue is subjected to flash chromatography on silica gel using a mixture of ethyl acetate and hexane as eluent. Concentration of the fractions yields the title compound as crystals, m.p. 89-90 ° C.

Example H22

Preparation of (E) -3,5-dichloro-1- (2-methylhex-1-enyl) thiatriazine

Analogously to Tetrahedron 1994, 5189-5202, from 16.43 g (0.2 mol) of 1-hexin, 310 ml (0.62 mol) of a 2.0 M solution of trimethylaluminium in hexane and 8.0 g (0 ZrCl ₂ (Cp) ₂ in 600 mL of dichloromethane prepared a solution of (E) -dimethyl-1- (2-methylhex-1-enyl) -lane. This solution was added dropwise over a period of 1.25 hours to a solution of 39.07 g (0.191 mol) of trichlorothiatriazine in 400 ml of tetrahydrofuran cooled to -40 ° C. Stirring of the resulting reaction mixture is continued cold for 1 hour, then 40 ml of water is carefully added at -30 ° C and the mixture is allowed to thaw slowly, with evolution of gas. The mixture is then filtered under vacuum through a pad of diatomaceous earth, the filtrate is extracted with water and washed with sodium bicarbonate solution to neutral pH and the organic phase is dried over sodium sulphate. Filtration and concentration of the filtrate gave a residue which was recrystallized from hexane. Crystals of the title compound of melting point 59-62 ° C are obtained.

Example H23

Preparation of 3,5-dichloro-1- (5,6-dihydro-4H-pyran-3-yl) thiatriazine

A solution of 61.3 g (0.3 mol) of trichlorothiatriazine in 600 ml of dichloromethane was cooled in an ice bath and 0.41 g of zinc chloride was added. To this mixture, 27.7 g of 3,4-dihydro-2H-pyran is slowly added dropwise with vigorous stirring. Stirring is continued for 1 hour, followed by the dropwise addition of 60 ml of triethylamine. Stirring of this suspension was continued for 0.5 hour at 22 ° C and the mixture was further filtered under vacuum. The residue is washed with ether, the filtrate is concentrated and water is added. After filtering the mixture, the residue is washed with water and dried. The crude product was subjected to flash chromatography on silica gel, eluting with dichloromethane / ether (1: 1). After evaporation of the obtained fractions, crystals of the desired compound are formed, which melts with decomposition at 127 ° C.

The compounds listed in the tables below can be prepared analogously to Examples H1 to H23. Abbreviations used in the tables have the usual meanings (Et = ethyl, Pr = propyl, i- = iso-, c- = cyclo-, t- = tertiary, s- = secondary, n- = normal).

Table 1

Compounds of formula I

NR ² R ³

Bile. 1

no.

R '

R ³

Physical data (melting point in ° C)

1.001 CK ₃ - -νή ₂ -och ₃ LCO-167 1,002 CK ₃ - -νή. -SC ₃ K ₇ (i) 185-136 1.003 ch ₃ - -nh ₂

ABOUT

185-137

1.005 ch ₃ - NH - CH ₃ -SC ₃ H ₇ (s) 116-117 1.006 ch ₃ - -nhch ₃ -och ₃ 153-154 1,007 ch ₃ - -NH-C ₃ H ₇ -OCK ₃ 123-130

F

CH ₃ -NH-NH-COOt-C 1

173-179

1.009 C ₂ H ₅ - -NK ₂

1-010 nC ₃ H ₇ -NH ₂

1.011 iC ₃ H ₇ -NH ₂

100

Bile. no. R ¹ R ³ <R ³ 1.012 n QHj- No, 1.013 C-C4H9- No, 1,014 T-C ^ - No, 1,015 C ₂ H ₅ No, 1016 ABOUT No, CH3 1.017 CH, No, 1,018 Q ch ₃ No, 1,019 ^{CH3 in} cK ₃ NH, 1,020 σ NH, 1,021 σ NH,

XR

Physical data (melting point in ° C)

213 solid solid

208 (decomposition)

171

101

Physical data (melting point in ° C)

Bile. no. R ¹ R ² Z ^N \ ^X R ³ 1022 σ -ΝΈπ 1,023 σ 0 -N H —-- 1,024 cr at \ ^ N \ = / 1.025 B-vCHcIá.- - * IH ₂ 1,026 i-RCK ^ u- -nh ₂ 1.027 NCSCCHt) * - -nh ₂ 1 1,023 IRL ° ° b -nh ₂ 1,029 (CH ₂ ) ₄ - N U -nh ₂ O- (CK ₂ ) ₄ - 1,030 s = o | -nh ₂ ch ₃

F ^ ^X F

-Q

F

D

.οΖΛ

181-132 (decomposition)

134-135

129-130

130

13i

169

232

-o / b

Pevná_ / solid o

solid

102

Bile. _R 1

no.

'R ^:

XR ^ Physical data (melting point in ° C)

L.031 HO- (CK2) ₄ - ₂ -NK

1.032

CK, S

-ΝΉ.

-O <3

1,033

NR ·?

r \

1,034

1.02:

1,036

S (C- ₂ j ₄ cC-H ..

i l

3 (CH ₂ ) ₄ I (Cr ₂ ) ₂ OH (C ₁ R ₁₅ S = O)

NH-NH,

-ABOUT·

O, ο-ΛΆ

English Translation:

-NR-,

-04 ^ solid

1,037

SO,

· NR.

210

1,038 O ₂ N (CK2) ₄ - NH 1,039 Cl - (CH,> NR 1,040 NC- (CH ₂ ) ₄ - -NR-

O solid

103

XR ^2,

Physical data (melting point in ° C)

R ²

Bile. no. R ¹ / ^N \ ^X R 1,041 C1- (CH ₂ ) ₄ - -nh ₂ 1,042 O (CH ₂ ) ₂ - (CH ₂ ) ₂ I -nh ₂ 1.043 NC- (CH ₂ ) ₅ - -nk ₂ 1.044 I-C4K9- -nh ₂ 1,045 nC _with H ₁₅ - -nh ₂ 1,046 nCH _l3 - -nh ₂ 1,047 (3-ch ₂ . -nh ₂ (CH ₂ ) ₂ - 1,048 Λ -nh ₂ at 1,049 in-CJV -nh ₂ 1,050 cCôHuCH.- -nh ₂ 1.051 O (CH ₂ ) ₂ - (CH ₂ ) ₂ Cl ₂ ; -nh ₂ 1,052 C ₄ H ₉ -CH ₂ - -nh ₂

-WITH-;

c-7

-J / \

-G

ABOUT

133

148

104

XR ⁴ Physical data (m.p. in ° C). R ¹

no.

i.os:

CH, -ΝΉ.

-O r \

C!

1.054 cC, Hn-OC- -NR

l.Ooo ¹¹

CH,

NR

1.056 cC4H, .CH _second NR

168-169 (decomposition)

141

158

1.057 tCl 2 R-OC- -NR

178-180 (decomposition)

RG 1053 and C ₄ = C-NR

1.059

C

III c

NR

CH- (CH ₂ ) ₃ 1.060 u ² ' ³ -NH ₂

163-164

105

Bile.

no.

, R ^ ^R3

XR

Physical data (melting point in ° C)

1.06 L

1.062

1,063

1,064

1,065

1,066

1.067

1,068

129

166

169-170

181-182

235> 240

106

XR ⁴ Physical data (melting point in ° C)

Bile.

no.

R ¹ /

^ R ³

1,069

NH,

1,075

1,070

1.071

1.072

1,073

1.074

136-137 nC ₅ H _n . -NH ₂

132-133

198-199

163-169

166-167

131-132

107

Bile. R ¹

no.

R ² /

Physical data (melting point in ° C)

1.076 n-C 1 -C 11 -NH-:

L.077 nC _: --H ·. - _L - -NH-)

1073 _n-C: H: _R NH ₂

1.079 QC ₅ H _n -NH ₂

1080 11-C5K ,, - NH ₂

1081 n-C ₅ H _{t R -NH2}

1.082 nC ₅ H _and -NH ₂

1083 n-CJH _the - NH ₂

174

140-141

180-181

227 (decomposition)

CH,

CH

159-161

135-136

137-139

153-154

108

R ²

Bile. R1 /

no.

Physical data (melting point in ° C)

1,034 nC ₃ K _ir -nh ₂ 1,035 nC ₅ K ·, - ies 1,036 nC ₅ K ,, - ies 1,087 n C5.n1., - ies 1.088 nC _ä H _u - ies 1,089 nC ₅ H, _r ies 1.090 CJK ^ n - ies 1,091 n-CJH ^ - ies 1,092 nC ₅ H _n - -Mi ₂ 1.093 nC ₅ H _ir -mi ₂ 1.094 nC ₅ H _u - -nh ₂

oc? ₃ 124-126

145-147

O O

solid

CHG / / C 3 ^h the solid

109

Physical data (melting point in ° C)

Bile. no. R ¹ of ^{R 2} \ _{r 3} 1.095 n CjKi - NH, 1,096 n CjKn- NH, 1.097 nC ₅ H _n - NH, 1,098 nC ₅ H _ir NH, 1.099 nC ₅ H _u - NH, 1,100 NH, 1,101 nC ₅ H _u - NH, 1,102 nC ₅ H _u - NH, 1.103 ⁿ 'QÄr NH, 1,104 nC ₃ H _ir NH, 1,105 nC ₅ H _tl - NH, 1,106 n-CjH _ir NH,

XR 7

L4S-L49

-O-C

-O-Cc;

100 (decomposition)

200 (decomposition) solid solid

110

Physical data (melting point in ° C)

Bile.

no.

R

FROM

N ^X R ³

1.107 π _2-5 Η, _- -ΝΈ solid _3c h

CHn

1.108 nC, -K _;

172-175

NH,

1.111 nC ₅ H _n -NH 2

Cooee

ABOUT

1.112 nC ₅ H 11 - -NK 11 -CK ₃

108-111 resin oil

155-156

ABOUT

1.113 nC ₅ H _n - -NH 1 --CH ₃

F oil

111

Bile.

no.

R ¹

^X R ³

Physical data (melting point in ° C)

1.114 nCK ,, nkA_ ch ₃

1.115 nC ₂ -H _ir. NH + -CH ₃

1.1 ló t f '-

-NH-CH x

CH,

CCCE

n-CÄ, -NH-CH, -COOE resin:

1.118

1.119 n-C, H, -NH-CH, -COOEc

-NH - CK ₃

1120 c C _s H _u - NH,

69-72

94-96

89-90

215-216 (decomposition)

1121 c C _s H _u - NH,

(Decomposition)

112

Bile.

no.

R ¹

^X R ³

XR ⁴ Physical data (melting point in ° C)

1122 cc _a .K, _r -NH ₂

185-186

1.123 cC ₅ K _n -NH ₂

106-208

1.124 C ₆ H, _r -NH ₂

1125 cc _and a _thickness H - NH ₂

I

ABOUT

ABOUT

C!

Cl

200-203

205-201

113

Bile. r1

no.

XR ⁴ 'RFysical data (melting point in ° C)

1126 c C _s H; _r -NH ₂

C

1127 c C _s A _{s -} NH ₂

1128 c C _s H _n - NH ₂

1129 c C _s H _{ir NH2}

1130 c C _s H _u - NH ₂

1131 c C _O H _{ir NH2}

F

English Translation:

COOEt

183-185

184-125

244 (decomposition)

125-126

114

Bile. R ¹

no.

R ²

XR ⁴

Physical data (melting point in ° C)

1132 c C _O H _{2 IRL} -NK

1133 c C _s H ,, - NH ₂

1.134 cC ₅ K, ₂ - -NK ₂

1135 c C _s H _u - NH ₂

1136 c C ₅ phi _u - NH ₂

1137 c C _s H _{r 2} -NK

1.133 c ₆ H _n -NH ₂

1139 c C _s H _r -NH ₂

1140 c C _O H _{ir NH2}

180-182

196-198> 240

202-205 solid

227

197-199

165-169> 240

115

Bile. _R 1

no.

Physical data (melting point in ° C)

1.141 c ₆ H _h -NH ₂

1142 c C _s H _{ir NH2}

_Delta H 1.143 c C ,, - NH ₂

1.144 c-C 6 H 11 -N -N ₂

1145 _C-NH2 CsHu-

1.146 cC ₆ H _n -NH ₂

174-175

235 (decomposition)

225 (decomposition)

202 (decomposition)

223 (decomposition)

1.147 cC ₆ H _ir -NH ₂

1.143 cC ₆ H _ir -NH ₂

220θ2 220 (decomposition)

(Decomposition)

116

Bile. R ¹

no.

^ R ³

Physical data (melting point in ° C)

1149 c C _s H _n - ₂ -NK

1.150 cC ₆ H _u - -ΝΉ ₂

1151 c C _s H _u - NH ₂

1152 c C _s H ,, - ₂ -ísH

1153 c C $ H, J = NH ₂

1.154 c-C 8 H 4 -NH ₂

1.155 cC ₆ H _n -NH ₂

1156 c C _s H _u - NH ₂

-WITH·

-s ^And s ^? nC _with K ₁₃ i

ABOUT

O i

CH, • CH,

et

ABOUT

235 (decomposition)

218 (decomposition)

153-154

193-194

Π7 ^R2 λ

Bile. R '/ XR ⁴

N

No. ^X R ³

Physical data (melting point in ° C)

1.157 c-CäE ..- -NEw. t _-

1153 C-Cxfí:, - _NH2

1159 c C _s H _ir -NE ₂

1.160 C-C.-E ,, · -NE

SCH.

1.161 c-CäH _u - No, 1.162 cC _ó H _u - -No.

/ \

cn ₃ s

OzScO

I

CH,

1,163 oCáHu- -ne ₂ 1,164 oCäHu- No, 1.165 cC ₆ H _ir -nh ₂ 1,166 cC $ H _n - -nh ₂

O i

CK ₂ (CF ₂ ) _With CF ₃

-O-CH _r CF ₃

-O-CH- (CF ₃ ) ₂

F F

OCH

157-159

131-133

140-142

150-151

Π8

R ^{2 Z1} R ¹ n ^Z XR ⁴

No. ^X R ³

Physical data (melting point in ° C)

167 cC _á H _tl - -nh ₂ -och ₃ 168 cC _with H _n - -nh ₂ -oc ₃ h ₇ (s) 169 c-CgKj i * -nh ₂ -OC ₅ H _n (n) 170 cC _á H _n - -nh ₂ -0-C ₆ H _h (c) 171 cC _á H _n - -nh ₂ -o-ch ₂ -ch = ch ₂ 121-124 172 ^c- c ₆ H _ir -nh ₂ -sch ₃ 177-178 173 cC ₆ K '- -nh ₂ S (O) CH ₃ 134-136 174 cC ₆ H _n - -ΝΉ. i » -S (O) ₂ CH ₃ 175 cC _á H ,, - -nh ₂ 206-207 (Decomposition) 176 -nh ₂ —NHCO -Q- 192-194 (Decomposition) 177 oC _á H _n - HC = CH ABOUT NH- 156-157 178 c-CsHn- sj = 0 MH bo - ° The 141-142 179 ^c 'QH _lt - ch ₂ -0 ^ 116-117

about

ISO cC ₆ H _u - NH-U-cci ₃

123-129

119

Bile.

no.

^X R ³ xsr

1.181

1,182

1,183

1,184

1.185

1,186

1.187

1,188

1.189

Physical data (melting point in ° C)

141-142

121-123

124-126

88-89

133-135

178-179

114-116

99-100

151-152

1.190 cC ₆ H '- 120 Comb. R ¹

R ²

XR ⁴ Physical data (melting point in ° C)

1191 C-1192 · CsHi c C _s H _n 1193 c C ^ Hn1.194 c C ,, H $ 1195 c C _s H _N H _O c C 1196 _IR

1197 c C _{n, and} a 1198 C-1199 C ^ GJH-CôHh1.200 c C _O H _in H

-NH —U — CH,

ABOUT

-NH - t - C, H _s

ABOUT

-NH - - - C ₃ H ₇

ABOUT

-NH-- C-C6Hg

NH-

-NH-CH ₂ C 10 O

-NH-thi-C ₃ H ₇ O

-NH 2 -nC ₄ H _g NH 6

The M

146-147

141-142

90-91

129-130

139-140

166-167 '° —126-127' ^0— 152-154 ° ^ ZZ ¹¹⁶

O-145-146

- 121 merger. R ¹

no.

XR ⁴

Physical data (melting point in ° C)

NH

1201 c C _{O N} H 1.202 c C ₆ H _ir

1203 H _O c C _IR

1.204 cC ₆ H _ir

1.205 cC ₆ H _ir

1206 c C ₆ H _n -

El

161-164

164-165

144-145

83-34 oil

84-85

73-74

1.207 cC ₆ H _at 122

Bile.

no.

R ¹

XR

Physical data (melting point in ° C)

1.208

1.209

1.210

C44-C ,. ^c — and — ti.

c-C, E '1.211 c-C.

1,212

1.213 c-CäEi i

1.214 c-CqK, j0

oil

61-63 oil

102-104

48-50

84-85

91-93 oil

1.215 cC _ô H _u 123

rl

N

FROM

Bile.

no.

'R ^:

Physical data (melting point in ° C)

1.216

1,217

1.218

1.219

1,220

1.221

1.222

1223 c-CJL p ^ ir c C _s H

The "C-cghj, ^c 'LL', and ^{a C} c C _s H, _R c C _s H _ir c-zag _in -

III / C

CN

Ch ₃ Diastereaner 1 O

Acf ₃

88-90

90-91

-N

CN

-ABOUT

CH ₃ diastereomer 2

UNC _{3H apos}

-N

CK ₃ - CH = CK ₂

N

NH-CN their ^

-about

92-93

- ° -o • θΌ

147-148

170-171 c ₆ H _tl -NH-CHyO-Ec

140-141

124

Bile. R

no.

XR

1,224 cC _á H _ir -nhch ₃ • ° Z2> 1.225 ch ₃ -NH - < CN diasterecmer 1 1.226 cC _ó H _u - CH, NH < CN diastereanér 2 • ° O 1.227 cC ₅ K _u - NH-CH-International 1,228 -nh-ch ₂ -ch = ch ₂ 1.229 OCH N / -NH-- ('7 n < ° O

OCH

1230 c C _O H _{£ 1} - NH - CH ₂ ZJ2>

1.231 c-CsH _ir

-NH-NH ₃ -CH ₃

-ABOUT

Physical data (melting point in ° C)

165-166

181-182

162-164

186 (decomposition)

182

147-149

130 (decomposition)

121-123

1.232 cC ₆ H _ir -NH-CH ₂ -CF ₃

125

R ² Δ

Bile. R ¹ / XR * ^N

no.

1233 C-CjHji1.234 c C ₅ H, C-1235 _L CJLv. 1

1236 c C ^ H ^ c C _delta H 1237 _II 1238 c C _s H _in H _O c C 1,239 _of 1240 c C ₆ H _with F

F

Physical data (melting point in ° C)

163-165

215-217

91-94

165-175

134-136

174-176

108-110 solid

126

Bile. rJ

no.

R ³ /

^ R ³

Physical data (melting point in ° C)

1.24 L cC ₅ H ,, ·

NH

-ABOUT

-about

117-118

NH ·

143-145

1.243 c-GEr

NH-XCH,

1.244 cC _á H, _r

_-NK-4-2 CKCí

-NH — H - CHCl3;

160-162

157-153

1.246 c-QH: _L-

NK - "- they want

-about

128-134

COCE

1247 cC ^ H, - NH (CK2) ₆ -NH ₂

F F

-oZý-F

F ^ F oil

1243 c C H _O N ^ _ir (CH ~ J ₆ -NH ₃ ^e C ^e 168th (dec)

F F

- NH (CH ₂ ) ₆ NHCOCtC _and H ₉ OF

F ^ F yawn

1.249 cC ₆ H _at 127

Bile. _R 1

no.

Physical data (melting point in ° C)

ABOUT

1250 c C _s H _N - _NH-2 XchCI

1251 c C _s H _{ir NH2}

1.252 cC ₅ H: - - ₂

H

r (diastereomer 1)

H

(diastereomer 2)

136-139 (decomposition)

200-202 (decomposition)

20i (decomposition)

165 (decomposition)

161 (decomposition)

164-165 (decomposition) (diastereomer 1)

128

Bile. R ¹

no.

Physical data (melting point in ° C)

1,260

1.25 ó

ABOUT

1.257

H

U '·>

1,253

U '>

1.259

Er

t u v

No. ₂ (diasKrecmér 2)

-ΝΈ (diasCrime 1)

-NE, (diasomer 2)

No,

F

- O °

Br ffV \ _F

NH,

1.261

br

U ''

NH,

157 (decomposition)

155 (decomposition)

177 (decomposition)

153-159 (decomposition)

176 (decomposition)

199 (decomposition) (diascersomer 1)

129

Bile.

no.

1.262

1263

1,264

1.265

1.266

1,267

1,268

1,269

1.270

nC ₅ H _n -ΝΉ ₂ ^η - <2 ₁₂ ΝΉις -ΝΉ ₂

CH ₂ CH (CH ₂ ) ₃ -nh ₂

Br Br ^c 'QHu -nh ₂ cC ₆ Hh -NH-NH ₂

Physical data (melting point in ° C)

201-204

CH

153-156

109-111

130

Bile.

no.

XR ⁴ Physical data (melting point in ° C)

1,276

1.277

1,278

1,271

1,272

1.273

1,274

1,275

CH ₃ (CH _{2) 4} CH ₂ CH ₃ .ηη

CH ₃ (CH ₂ ) ₄ CH-NH ₂ CH ₃

CH ₃ (CH _{2) 3} CH ₂ CH ₃ .nh

224

221

165-166

127-128

143-144

117-122

166-167

131

Bile. R?

no.

Physical data (melting point in ° C)

1,279

C! * 2'3 ^C '

-ΝΈ.

1,280

I c:

1281 n C _s H _I7

-ΝΉ.

-NH ₂

167-169

105-106

1232 n-C _{3 E:} 12283 QC _{to H, 7}

-NK ₂

1.284

-nk ₂

1.285 nC ₁₂ K25

-nh ₂

1.286 c-C18 n

-NH- (nC ₆ H ₁₃ )

120-121

114-115

121

110-111

105-107

132

Bile.

no.

R ¹

^ 4 Physical data (melting point in ° C)

1287 c C ₆ H _tl -NH-N = CH (CH 2) ₃ CH ₃

1.288 cC ₅ H _at -NH-N = CH-phenyl

1,289

1.290

1.291

1.292

1293

114-116

229-231

237-239

120

161-162

133

Bile. R ¹

no.

Physical data (melting point in ° C)

1,294

-NH ₂

-ΝΉ;

-ΝΉ-, isomer 1

-about

-OCH - CN

-ABOUT

F

146

135-137

200 (decomposition)

1.297 -ΝΈΓ »

C-CCCK.

isomer 2

195-196

1.298 í

C-CCCH.

No?

1.299 isomer 1

isomer 1

Sr

-NE

O-CCCH,

-O (decomposition)

1,300

OC, Hc:

-NE>

2''5

1.301 nC ₉ H ₁₉

No,

183 (decomposition)

175 (decomposition)

190 (decomposition)

81-82

134

Bile. R ¹

no.

XR ⁴ Physical data (melting point in ° C)

F

(E)

135

Cmpd

no.

R ¹

ΕPhysical data (melting point in ° C)

1.310

1.311

1,312

1.313

1,314

1,315

1.316

1.317

1.318

-nh ₂

Λ »- NH, T ₂ &lt; ₅ n-C ₄ Hg

_.Λ ^η - -NH

C ₂ H ₅ n C ₄ H ₉

CjHg

^Λ η - NH, (CH _{2) 2} -, -NH (CH _{2) 2} - -NH-, © - ^ICH ^ 'c C ₆ H _n

-NH ₂

-nh ₂ n C ₈ H ₁₇ -NH (CH ₂ ) ₆ NH ₂ (CH ₃ SO ₃ H) ₂

F F

182-133

F F

133-137

153-reg

182-183

127-130

167-163

189-190

-OCH, CCl, CF ₃ 188-190

124-125

136

Bile. r1

no.

RFysical data (melting point in ° C)

1.3L9 _Cc Ki; 1.320 cC ₅ H =,

1.321 cC _á H ,:

CH ₃

I

1.322 CK (CK ₂ ) 5 CHq

I

1.323 CH (CH 2) 5 CHt

CK ₃

I

1.324 CH (C 1 -C 12) 5 * -1.0.3 nh ₂ nk ₂

The

-N- (CK ₂ ) ₅ -COO ^e Na ®

-OCH ₂ (CF ₂ ) ₂ Cr ₃

-OCE ₂ CF ₂ CF ₃

F

159-160

145-146

150 (decomposition)

-ΝΉ-.

-NH ₂

-νή ₂

1.325 Cl-CCH 2 s-nh ₂

1.326 C ₂ K ₅ O

-NHi

4th

CK,

1.327

Pr

-nh ₂

113-114

134-135

F

119-120

162-164

143-144

F

143

137

Bile. R ¹

No.

/ ^ R ³

Physical data (melting point in ° C)

1,328 CH. 'Pr -nh ₂ 1,329 CH, CH -nh ₂ (C »^ 1.330 ch ₂ = ch 1 -nk ₂ - (C -i,) .. 1,331 C n, - \> R '1 - {C i ₂₎ 4 -nk ₂ 1.332 nC ₅ K _L1 H N ^ CHfgNH, 1.333 c ₄ H 9 -CH _r (CH ₃ SO ₂ H) ₂ - ₂ 1.334 cC ₄ H9-CH ₂ - -νή ₂ 1.335 c-QHg-C ^ - -nh ₂

144-152

116-118

144-145

170-172

184-185

140-141

F

F

138

Bile. R ¹

no.

X R * ’Physical data (melting point in ° C)

1.336 c-C 8 H 11

1,337

O-Z diasteromer 1

1.338 nC ₃ H ₁₇

OCH ₃ Coch ₃ nh-Coch ₃

NH-COCH

_-NH-COCH3

1342 4-Cl-C ₆ H ₄ -NH ₂

F F

o M-f

95-97

157-158

94-95

100-101

223 (decomposition)

180-184 (decomposition)

182-185

F

F

139

ziúč. R ¹

no.

XR ^ Physical data (melting point in ° C)

1.3-NH, k ₂ n - //

-ΝΉ-.

1.345 nCiHgOCH = CH- -NK ₂ (Z)

1.346 nC, KcOCH = CH- -NH ₂ (Z)

1.347 nC ₄ HgOCH = CH- -NH ₂ (E)

1.348 nC, H9OCH = CH- -NH ₂ (E)

1.349 nC ₄ H ₉ OCH = CH- -NH ₂

(E)

140

Physical data (melting point in ^e )

Bile.

no.

1.350 (CH ₃ ) ₃ Si (CHt) ₃ - -ΝΈ,

1.351 (CH ₃ ) ₃ Si (CH ₂ ) ₃ -NH ₂

1.352 (CK ^ SiCCH ^ - -ΝΉ,

1.353 CH ₃ O 2 -NR,

1.354 CH ₃ O - NK

1.355

1,356

1,357

-NH ₂

-nk ₂

-NH _z

141

Bile. ^r1

no.

Physical data (melting point in ° C)

142

bile. R ¹

no.

R ²

X r ² »Physical data (melting point in ° C)

1.365 I-C ₄ Kg -nhnh ₂ 119-120 1.366 c-CqHh -N (CH ₃ ) ₂ F -och ₃ oil 1.367 cC ₅ K _n -N (CH ₃ ) ₂ -S-C ₃ H ₇ oil 1.363 oC ₅ H _{h 2} -S-C ₃ H ₇ resin 1,369 ^c-C 6 ^h il -NH-N = CH-C ₃ H ₇ -S-C ₃ H ₇ 69-70 1,370 -NH-OH -S-C ₃ H ₇ resin 1.371 cC _á phí _ti -NH-nC ₃ H ₇ -S-C ₃ H ₇ 73-74 1,372 c-CóIxíi -NH, \ and ₃ -S-C ₃ H ₇ 172-173 1.373 c-CóHh -S-C ₃ H ₇ resin 1.374 Br- (CH ₂ ) ₅ - -nh ₂ 116-118 1.375 I- (CHT) -5- -nh ₂ - O ° 118 1,376 C 1 (CH _{2) 5} - -nh ₂ - ° The 125 1.377 n CjKu -nh ₂ -OnC ₃ H ₇ 75-76 1.378 ch ₃ - och, N- ( ^3- NH-CO-) and _{3 -O-CH3} 1,379 N'eCSíCH ^ s- -nh ₂ - ° o 143 1.380 CH ₃ COO (CH ₂ ) ₅ -nh ₂ - ° The solid 1.381 <γΖ ^ ~ ^S '< ^ch 2> 5 -NH ₂ - O ° solid

143

Bile. R

no.

N,

Physical data (melting point in ° C)

1.382 cCýKuS (CC ₂ ) ₅ - -nh ₂ - O ° solid 1,383 -nh ₂ -about 124-125 1.334 cC ₄ K ₂ -CH ₂ - -NH ₂ .Q 142 1.335 CK-CK ^ ^ tCK - -NH ₂ 154-155

GC, HI

1.386 C == s S- (CK ₂ } .1.387 NaOqSSCCH 2 -NH ₂ n - // v

166-163

220

1,383 C ₁ H ₂ -Sr C 1 -C 15 (C 12/2 -1433.-, 146-150 1.389 HS-CH ₂ -NK ₂ --- Q 116 1.390 KoNCiCF ^ S ^ C.-i ^ L- -NH, CGCH -about 183-135 1.391 CH ₃ CH-C ₃ H ₇ -NH ₂ ° o 152 1,392 (CjHtNHCCHi) n -nh ₂ 115

1.393

-NH ₂

F

F ΐ 44

Bile. ^R

no.

XR ⁴ Physical data (melting point in ° C)

1,401

145

Bile. ^r1

No.

N.

R ²

Physical data (melting point in ° C)

1.402 cC ₅ K _for -NKOC ₂ H ₅

1.403 nC ₅ H _H -

1.404 c-C11, -ΝΉΟΗ

CH1.405 nC ₃ H ₇ -Si - (CH ₂ ' ₃ - -NH ₂ ' ₎ CH ₃

1.406 nC ₃ H _r Si- (CH ₂ ) ₃ -NK, C ~ ₃ CH1.407 n C ₃ H ₇ -Si (CH ₂ ) ₃ -NH ₂

CH

1408 Br-CH ₂ - NHCOCH ₃

1.409 Br-CH · - -NH-

NC

146

Bile.

no.

XR ⁴

Physical data (melting point in ° C)

CF,

1.410 cC ₆ H _n

1.411 C1-CH ₂ 1.412 CH ₃

1.413 CH ₃

1.414 cC _ó H _n

1.415 I-CH ₂ 1.416 c-CsH _n

1417 _CH2 = CH1.418 _CH2-CH-NH-C (CH _{3) 2} -CsCH

-νή ₂

-nh ₂

-nh-coch ₂ cooch ₂

-ABOUT

-ON = Cl (C ₃ H ₇ ).

F

- ~ -d>

F

147

Bile.

no.

Physical data

XR, (melting point in ° C)

CCCH

1.419. C-C-H:;

vjk ... ^T r 'c: -i ,; ₄ -nkccc (c ₄ h ₃ ) -O

1.420 c-Cl

NH, CH; _t j «CCCH

NKCCClt-C ^ H)

-ABOUT·

1.421 c-R

-NR (CIR) ₅ -COOH

1.422 c-C £ '

-NH- (CR), - COO ^C. For ^E

-about

1.423 (CRRSi-CR- -NR

1424 (CR) ₂ CK (CR) ₂ -, -NR

F

-O <7

140 ° C

148

Table 2

Compounds of formula IV

Bile.

no.

C!

(IV)

Physical data (melting point in ° C)

2.001 CH ₃ - 101 (decomposition) 2.002 c ₂ to ₅ - 107-108 (decomposition) 2.003 nC ₃ H ₇ - 2.004 iC ₃ í ₇ - 2.005 nC ₄ K ₉ - 43-44 2.006 cC ₄ Hc- (CH ₂ ) _d - 2.007 T N

2.008

2.009

CH,

CH,

CH,

2.010

2.011

2.012

2.013

CH,

CH,

CH ₃

127 (decomposition)

14s

Bile. R

no.

Physical data (melting point in ° C)

2.014 I- (CH 2) ₄ 2.015 NCS (CH 2) ₄ (CH ₂ ), -

(CH ₂ )

O- (CH ₂ ) ₄ 1.018 C = O

I ch ₃

2.019 (CH ₂ ) ₄ - d ₃ c-š 2.020 -S- (CH ₂ ) ₄ - 2,021 S (Cr ₂ ) ₄ - c-H _n 2.022 C1- (CH2) ₄ - 2.023 NC- (CH ₂ ) ₄ - 2,024 NC / CH), - 2,025 2026 nC _ó H ₁₃ - 2,027 CYH ^ n - 42-43 2,028 O ^- “ ² ' 137-138 (decomposition) 2,029 (CH ₂ ) ₂ - 92-94

about

2.030 sC ₄ H ₉ 2.031 cC ₆ H _for CH ₂ 97

150

Bile. - ^x no.

Physical data (melting point in ° C)

73-74 oil

130 (decomposition)

91-94

96-97

151

Bile. R ¹

no.

Physical data (melting point in ° C)

OH

2.046

t-C.Hg 2,047 HO- ^ ~ ch ₃ c> 2,048 nC ₅ K ,, - 2049 cC _á H ,, - Er

2,050

105-106

/ '(/IN

L27-1Z

2.051

2,052

2.053

ΟΛ och ₃ nC _L2 H

CH ₂ CH (CH ₂ ) 3

51-52

2.056 and ₃

152

Bile.

no.

Physical data (melting point in ° C)

2,057

2.058

2.059

2,060

2,061

2.062

2.063

2.064

2.065

2,066

2,067

2.06S

2.069

Cl

F oil oil

CH ₂ (CH ₂ ) ₄ CCl ₃

CH ₃ (CH ₂ ) ₃ CH ₃ nC ₃ H ₁₇

116-119

Π-C ₈ H 11 g n C ₁ H ₃ H

125 (decomposition)

54-55

59-62 h ₃ c (E) n C ₄ n ₉ / CH - C ₃ H 8 ch ₃ ^ Η (Οπ'2) 5Oh ₃

C 1 (CH _{2) 5} -

iPr oil

38-40 oil oil

153

Bile. R ¹

no.

Physical data (melting point in ° C)

CH = CH 2

2,070

2.071

2.072

- (CHJ t-C H -CH

9 2

48-51 oil

Q>

2,073 nCH 0CH = CH- 4 9 (FROM) 2.074 nCH 0CH = CH- 4 9 (E) 2.075 (ch ₂ ) ₃ si (ch ₂ ) 2.076 Cf Q ³ ° _w - 2.077 ^C1 -O F ŕ 2.078 2,079 Br- (CHJ _with - 2,080 I - (CH) - 2.081 N = CS (CH) - 2.082 CH ₃ C00 (CH ₂ ) _s -

• S-Cr oil

111-112 (decomposition)

77-78

107-109 crystals oil

2.083

2.084 cH H (CH) 2.085 N - (CH) 2.086 C-C H -CH 4 7 2

2.087 CH = CH- (CH) 2 '2 * 2

CH-Br 2

2.088,

CHBr - (CH) 2.089 CH CH-IC 3 H 3

154

Bile.

no.

R ^x

Physical data (melting point in ° C)

2,091

2.092

2,093

2.094

2,095

2.096

2,097

2,098

2,099

2,100

2.101

2.102

2.090

144-145 crystals crystals n-C H - Si - (CH) 3 * 7 '2'3

CH

Br-CH2

Cl-CH 2 i-CH ₂ CH = CH ₂ C H e XX (CH ₃ ) ₂ CH (CH ₂ ) _and -

crystals crystals crystals

73-76

73-76

155

Bile. R ¹

no.

Physical data (melting point in ° C)

103 L í J 104 Chis-vCKt); - 105 č '' -, - (CH ₂ ) j - 106 c ₂ to ₅ o-want ₂ - 107 nC, E _r O-CECl-CH ₂ - 108 l-C ^ O-CHCl-CE - 109 (E) C ₂ H ₅ O-CH = CK- 130 (decomposition) 110 (3C and CE-O = CH- 87 i 11 The destination CEA-CE = CH 109-110 (decomposition) I T? (Z) i-C ± ejo-CH = CH- oil 113 rr crystals

Q Cl

100 (decomposition)

2.115

Cl

2.1 L ó F-CH ₂ 2.117 CH ₂ = CC-CE ₂ 2.113 CH _r CC = CH-

crystals

134-135 (decomposition)

OCH

-C

2.121

156

Bile. R ¹

No.

Physical data (melting point in ° C)

2,122

Cl

2.123 oe oil 2,124 (Z) C ₂ H ₅ O-CH = C (CH ₃ ) - 115 (decomposition) 2.125 (E) C ₂ H ₅ O-CH = C (CH ₃ ) - 94-95 (decomposition)

57

Table 3

Compounds of formula VI

Bile.

no.

XR ⁴ Physical data (melting point in ° C)

3.001

3.002

3.003

3.004

3,005

3.006

3.007

3008

3.009 nC ₄ H ₉ 158

X R * Physical data (melting point in ° C)

3.020 Br (CH3) d159

ZIÚC. R

no.

Physical data (melting point in ° C)

3.021 1- (0¾ ..

.022 NCStCK- ^ 3.023 (C., ₂ ) ₄ o ^ ^N ^ = o

3.024 (Cn ₂ ) ₄ N

ABOUT

3.025

- (C.- ₂ ; ₄ CQ

CK ₃

3026 KO- (CH ₂ U-

3.027

3.02S (CH ₂ ) ₄ ch ₃ s (CH ₂ ) ₄ I s

3.029 S (CH ₂ ) ₄ CC _S H ,,

3.030

S (CH ₂ ) ₄ (CH ₂ ) ₂ OH

160

Bile. R

no.

Physical data (melting point in ° C)

3031 (CH _{2) 4} S-O

_{(CH2) 4-1} 3,032 Sat ₂ 3,033 O ₂ N (CH ₂ ) ₄ - 3034 C1- (CH ₂ ) ₄ - 3.035 NC-CCK ^ - 3,036 CHCH ^ U- 3,037 O (CH ₂ ) ₂ - (CH ₂ ) ₂ I 3.03S NC CCH ^ s- 3,039 iC ₄ H9- 3.040 nC ₆ H ₁₃ 3.041 nC ₇ H ₁₅ -

161

XR ⁴ Physical data (m.p. in ° C). R ¹

no.

3.042 ' _to C — 2 <' 2 '3.043 ¹ // \

with

SCE 5044, 3045 cCEuCH, C (CH _{2) 2} j.046 (c: ies _{2) 2} C

3.047 iCiKn-CH

3.049 cCHg-OCch-ch ₂₃ 3.050

CH ₂

3.051 cCgH ^ CK, 3.052 tQHg-OC-

162

XR ^ Physical data (melting point in ° C)

Bile. ^R

no.

3.053 nC ^ R-C ^ C-

3.054

C

III

C

3,055

5056

CH (CH,), II

CH,

CH _{(CH2) 3} II

CH,

3.057 cC ₆ H ₁₁ CH,

3.05S cCsHuCR3.059 cC ₃ H ₉ CH ₃

3.060 ^ho v3 ~ CH

163 „1

Bile. R

no.

Physical data (melting point in ° C)

3,061

3,062

ABOUT

-Q

3.063 ^CH3 d ^X

3.064 nC ₅ H, _r

3.065 nC ₅ K _n 3.066 nC ^ Hu *

3.067 nC ₅ H _tl 3.06S nC ₅ H _ir

3.069 nC ₅ H _ir

C

164

Bile. ^R

no.

XR

Physical data (melting point in ° C)

3.070 nC ₅ H, 3.0 / 1 n-C ₁₁ H, 072 n C ₅ H, _r

3073 aC. _IL-H 3074 n-C ,, H 3075 n-C ₅ H: _R

3.076 nC ₅ H _ir

3.077 nC ₅ H _tl 3.078 n-C ₃ H 4 3.079 n C ₅ H _ir

resin

165

Bile. no. R ¹ 3,080 nC ₅ H ₁ 3081 nC ₅ H, _I - 3082 nC ₃ K _ll - 3,083 nC ₃ H _u - 3084 nC _f K _ir 3.085 nC ₅ H _ir

Physical data (melting point in ° C)

3.086 nC ₅ H _ir 3087 nC ₃ H _{£ 1} - 3.088 nC ₅ H _ir 3089 nC <H _££ - 3.090 n- _{C 1} H _{£ 1} - 3,091 n CjHn- 3092 ^{n C 1} H [i-

-OC ₃ phi ₇ (i)

-o-ce ₂ -ck = ce ₂

-oc-cA ch ₃ /

CH.

Λ

-0 Η _π (η)

HO

166 zlúč.

no.

XR ⁴ Physical data (melting point in ° C)

3.093 nC ₅ H _u 3.094 nC ₅ H _n 3.095 nC ₅ H _u 3.096 nC ₅ K _ir

3.097 n-C 11 H 11;

3.098 nC ₅ H _ir

3.099 nC ₅ H _ir

3.100 cC ₆ H _Ll

F

167

Bile. ^R

no.

χρΑ Physical data (melting point in ° C)

Ο)

C

168

Bile. ^R

no.

XR ⁴ Physical data (melting point in ° C)

3.106 cC ₆ H _ir

C!

3107 c C _s H _{t R} 3.108 C-c-CáHu3.109 CgHu3.110 c C ₆ H _ir

3.111 cC ₆ H _u r

130 (decomposition)

CCCE:

resin

169

Bile. R ¹

no.

XP ² - Physical data (melting point in ° C)

CO CO CO CO _to H c C .112 .113 _{ir ir} c C _O C .114 _Cc to _the • Π5 c C _s H _n 3116 c C _s H _N H 3.117 c C _{o n} c C ₅ H 3118 _of 3119 c C _s H _r

3120 H _O c C _IR

F resin

170

Physical data (melting point in ° C) combined. R

XR *

no.

3122 H _O c C _IR

3123 c C ₅ H _{.mu.l of} 3124 cc _{and a} C _of 3125 c C & i3.126 QH-C,? 3127 c C ^ c C ₆ H 3.128 _in -

171

Bile. ^R

no.

XR ⁴

Physical data (melting point in ° C)

3.129 cC ₆ H _ir

3.130 cC ₆ H _ir • 131 cC ₅ H _n 3.132 cCa, 3.133 cC ₆ H _ir

3.134 c ~ C ₆ H _ir

3.135 cC ₆ H _at 3.136 cC ₆ H _ir ' ^C y_ / ^C1

CH,

C-

CH,

ΓΠ

C-N

II

ABOUT

u. · '3

-WITH'

N

ABOUT

172

Bile. R ¹

no.

XR ^ Physical data (melting point in ° C)

3137 c C ₆ H _at 3138 c C _s H _n c C ₆ H .139, .140 _R c C ₆ to 141 _n • c C _n H _with the U2 c C _s C c C _{o n} .143 H _at 3144 c-c-CGH QHu3.145 .j3.146 cC ₆ H _ir

3.147 cC $ H _u do it do it do it

br

CH-> S o = ltd i

ch ₃

ABOUT

I

Crl ₂ (CF ₂ ) ₆ —cf ₃

-o-ch ₂ -cf ₃

-O-CH- (CF ₃ ) ₂

F F

-cch ₂

-och ₃

173

Bile. R ¹

no.

Physical data (melting point in ° C)

O) OJ

3.14-3 cC ₆ H _; 3. L 49 3.L50 QH-C: - 3.15 L C-CJK :: - 3152 cC _á H _ti - 3.153 QK-C,; - 3.154 c-QHu-

-OC ₃ H ₇ (i)

-OC ₅ H _n (n)

-OC ₆ H _n (cy.)

-o-ch ₂ -ch = ch ₂

3155 c-Cai, - 3.I5Ó cC _á H _ir 3157 cC _á H _n - 3.158 c-Çakır

o7

174

Physical data (melting point in ° C)

no.

3.161 ^S O

OCH ₃

Er

XR

3.162

3163

3164

3.165

3166

3.167 'c-C 1

II-C5H1 j

Π-C {2 ^ 25

CH 2 CH (CH 2) 3 Br Br

175

Bile. ^R

no.

Physical data (melting point in ° C)

OJ OJ OJ

3173 CH ₃ (C n _{2) 4} CH ₃ CHCH3.174 (Cri _{2) 4} H CH ₃

3.175 CH ₃ (CH ₂ ) ₃ CH ₃

3.176 CH ₃ (CH ₂ ) ₃ CH ₃

3.177 CH ₃ (CH ₂ ) ₃ CH ₃

3.178 nC _with H ₁₇

176

Physical data (melting point in ° C)

Bile. ^r1

no.

it t ^r i do it do it do

F

i, Physical data

Bile. R ^NR4 (m.p. ^No · ° C)

3.189

3.190 n-CgR

3.191 n-CglR

3.192 n-CjH ^

3.193 nC ₇ H ₁₃

3.194 nC ₇ H ₁₅

3.195 nC ₇ H ₁₅

F

178

Physical data (melting point in ° C) combined. R ¹

no.

179

Physical data (melting point in ° C)

Bile.

XR ⁴

3205 Qr _(CH2)

3.206 c-C, ι

3.207 nC ₃ H; ₇

3.208 cC, H _L1

3.209 c-CH ₁ CHI

3.2. and

CHH

-OCK ₂ (CrJ ₂ CF ₃

-OCH ₂ CF ₂ CF ₃

it

2Π

CH ₃

CH (CH ₂ ), CH ₃

CH3.2 L2 CH (CK ₂ ) ₅

F

180 "1 string. R

no.

XR

Physical data (melting point in ° C)

3.218

3.219 ch ₂ = ch

I

- (CH ₂ ) ₄ ch ₂ = ck

I

- _{(CH2) 4}

3.220 cC ₄ H9-CH ₂ 3.221 tC ₄ H9-CH ₂ F

w

3.222

181

Physical data (melting point in ° C)

Bile.

no.

F F

3.227 4-CI-C5H4.

3.228 nCJ ^ OCH ^ H (Z)

3.229 nC ^ OCH ^ Si-

(FROM)

182 ziúč. R

no.

Physical data (melting point in ° C)

3.230 _± HcOCH n C = CH (Ξ) = ECCH NCL-CH132 nCaHcOCH CH3.233 = .234 (CE _{3) 3} Si (GL) ₃ 3.235 (CK _{3) 3} Si (GI2) ₃ 3.236 CH ₃ O ^ J ^

F

183 ziúč. R

no.

Physical data (melting point in ° C)

* iC ₃ H ₇

3.242

3.243 iC ₄ H ₉

3.244 cC ₆ H _n .

3.245 Br- (CH2) ₅ 3.246 I- (CH2) ₅ -

184

Bile. no. R ¹ 3,247 C1- (CC ₂ ) ₅ - 3243 nC ₅ K _u 3249 NonCS (CK2) ₅ - 3,250 CK ₃ CCO (CK ₂ ) ₅ - 3251 θ-S ^ ick. 3252 cC ₅ H _n S (CH ₂ ) ₅ - 3253 N ₃ - (CH ₂ ) · 3254 cC ₄ H - CH ₂ - 3255 CH ₂ = CH- (CH ₂ ) ₂ - CH ₂ -Sr 3256 óncrf ^ Cr ^) ^ 3257 ch ₃ ch.ic ₃ h ₇

XR

Physical data (melting point in ° C)

WHAT

185 ziúč. ^R

no.

XR ⁴ Physical data (melting point in ° C)

Er

3.267 nC ₅ K _n

F

186 ziúč. R č.

Physical data (melting point in ° C)

3.263 cC _á H _t ,

C .. ₃

3269 n-C ₃ C - Si, CK ₂₎ CH _3,

CH,

1 /

3.270 nC ₃ H ₇ -Si (CH ₂ ) ₃ ·

CH, ch ₃

3.271 nC ₃ H _r Si- (CH ₂ ) ₃ ! H ₃

3.272 Br-CH, 3.273 Br-CH, 3.274 Cl-CH, 3.275 I-CH, F

'° \\ // \\ / 7

187

Bile. R.

no.

Physical data (melting point in ° C)

F

188 '1

Bile. ^R

no.

Physical data (melting point in ° C)

OCH

-u oil oil oil

189

Table 4

Compounds of formula VIII

R

NFČr ³ (Wine)

Bile. r ¹

no.

Physical data (melting point in ° C)

4.00 L CR- NR 154 (decomposition) 4.002 CR- -nhce ₃ 135-136 (decomposition) 4.003 Cr- -NH-ICR 120-122 4.004 Cr- -NE-NK-Cocci-RR 180 (decomposition) 4.005 c ₂ r- NR 160 4.006 nC ₃ K ₇ - NR 4007 iC ₃ H ₇ NR 4.008 n-RR- NR 4009 c-C.R- NR 4,010 ^c - ⁵ R / NR

4.0 II -NR

190

Bile. R ¹

no.

Physical data (melting point in ° C)

4.015 NH. 4.0 ló BrCC ₂ ) ₄ - -No. 4017 I- (CK,) _4- NH. 4.018 NCS (CH> -No. (C ₂ ) ₄ - 4,019 o ~ V ° about NH. 4,020 (CH ₂ ) .- 1 N U No, 4021 0 - (CC ₂ ) ₄ Czo I -nh ₂ CH 4,022 KO-CCHJ - No, 4,023 (CH ₂ ) ₄ -; C No,

181 (decomposition)

4,024 ABOUT NH, 4.025 S (CH ₂ ) ₄ - CC 8 H, S (C ₂ ) ₄ - NH, 4.026 1 (CK) ₂ OK NH,

191

Bile.

no.

R '

The physical data (melting point in ° C) (CH _{2) 4} I,

4027 s = o about -NK. 4,023 (CH ₂ ) ₄ - 1 Sat ₂ NH, 4029 0 The N'CCK ^,) .- -NK. 4.030 C1- (CH ₂ ) ₄ - NH, 4031 NC- (CK) _d - NH, 4,032 CI- (CK,) _d - -NK. 4033 O (ch ₂ ) ₂ - NH, 4.034 (C. ' ₂ ) ₂ I NC- (CH3) _S - NH, 4.035 i-CKg- NH, 4.036 n-CaH ₁₃ - -NK. 4.037 nC ₇ H ₁₃ - -NK. 4038 ABOUT*' NH, 4039 (CH ₂ ) ₂ - Λ NH, 4,040 M sC ₄ K ₉ - NH, 4041 cC ₆ H _u CH, - NH, 4.042 O (CH ₂ ) ₂ - -nh ₂ 4043 (CH ₂ ) ₂ Cl ₁ C ₄ H ₉ -CH, - NH,

173 (decomposition)

192

Bile. ^R

no.

Z \ _T

Physical data (melting point in ° C)

ch ₂ - 1 4044 n -nh ₂ s C ' 4,045 tQHg-OC- -mh ₂ 155-153 (decomposition) 4,040 C.-.- _{(CH2) 3} - _CH2 -nh ₂ 119-120 4.047 II c ^ -OC -nh ₂ resin

4043

-ΝΉ-, resin

C i

4.049 cC ₅ H ₉ -ΝΉ-,

4.050

CRTG

HO ^ -ΝΉ,

CH

4.05 L

4052

4053

CH.

HO

CH ₃ O

4.054 HO

-ΝΉ ₂

-nh ₂

-nh ₂

-nh ₉

180 (decomposition) ch ₃ o

193

Bile. R ¹

no.

Physical data (melting point in ° C)

4.055

CH, OH

B-NH

CH,

CH,

4056

Ho- ^ y

NH,

CH

4.05 / -NH ₂ r-Γ ^L HO-ý ”\ - 4053 -nh ₂ ch ₃ o 4059 nC ₅ K, _r -νή ₂ 4.060 nC ₅ H _n - NH - <(

139

COCE

CH, / ⁴

4061 nC ₅ phi, _r NH-CH \ θΟΕί 4062 -NH-CH ₂ -COOEt 4063 oCA- -ΝΉ-. L, 4.064 ^c _-Ca H _ir W 0 4065 c C _O H _R -NH- _(CH2) 3-CN 4066 cC ₆ H _{ir NH-CH2-O-Ec} 4067 c-CôHu- -nhch ₃

194

Bile. ^r1

no.

R ¹

R

Physical data (melting point in ° C)

4068 4069 c C ₅ H _u - c C _s H _n - CH ₃ -NH- / CN -NH-CH 2 -OCH 4.070 ^c- ₅ h, _r CK -NH-, -CH = CH, N f ₃ CCK 4071 cC ₅ H, i- -NH ý CC r .. 4072 c C _s H, _R -NH-CH ₂ —Q Q 4073 cC ₆ H _u - -NK-NK - ^ - CH, 4.074 cC ₅ H ,, - -NE-CH ₃ -CF ₃ 116-118 4.075 C-car -NK-NK-COOt-CiEg 195 (decomposition) 4.076 cC _á H, _L - -NH- (CK) ₆ -NK, 4.077 cC _á H _it - -NH (CH 2) ₆ -NNE, C 1-6 4.078 cC ₅ H _u - - NH (CH _{2) p} NHCOCtC .H, W ivica

□ r

4.079 I -NH,

130 (decomposition)

4.080 ⁰ OCK ₃ -νή. 4081 n-C ^ H ^ NH, 112-113 4,082 CH ₂ CK (CH ₂ ) ₃ i 1 Br Br NH, 4083 cC ₆ H _t . NH-NH, 136 (decomposition)

Cl

4084

NH,

0 and ₃ crystals

195

Physical data (melting point in ° C)

Bile. R ¹

no.

CI

4087 Í. 1 IN\ Q -νή ₂ 130 (decomposition) 4083 : / ru \ '• -j T -νή ₂ 93-95 ch ₃ 4,089 CK ₃ (CK ₂ ) ₃ -nh ₂ 118-120 (decomposition) CK ~ 4.090 -ne ₂ 113-114 4.091 C ·% -NH- (nC ₅ H ₁₃ ) 58-60 4092 C -C _á H :, NH ^ C ^ ^ Chico 4093 C -r.p .. -NH-N = CH-Ph 4.094 -nh ₂ 146-151

135 (decomposition)

4.096

Si _{(CH3) 3}

-nk ₂

195 (decomposition)

196

Physical data (melting point in ° C)

Bile. R ¹

no.

4.097

NH,

124 (decomposition) cc ₂ h ₅

4098 n— ₉ -nh ₂ 108-109 4099 H-C / H H -nh ₂ 126-127 4,100 \ - / / \ H, C \ ŕc'í -nh ₂ 118-120 4.101 -about N-C., Kc -nh ₂ 4.102 c ₂ K ₅ -nh ₂ 100-110 4.103 'yľ / (£ η ₂ ) ₂ - -nh ₂ 170 (decomposition) 4.104 nC ₃ H ₁₇ -NH (CH ₂ ) ₆ NH ₂ (CH ₃ SO ₃ K) ₂ H 4.105 cC ₅ K _u ch ₃ -N- (CH ₂ ) ₅ -COO ^e Na ^e 4.106 CH (CH ₂ ) ₅ - ch ₃ -nh ₂ 130-131

crystals

4.107

4.108

4109

143 (decomposition)

155 (decomposition)

197

Bile.

no.

R

Physical data (melting point in ° C)

4.110

4.111

4.112

4,113

4.114

4115

4.116

4.117

4.118

4119

4.120

4.121

4.122 * -NE, 124-126

H

N (CH _{2) Z} NH (CH ₃ SO, E) ₂

t-Chg-CH, - -No. ABOUT' No. 171 (decomposition) 4-Cl-C £ _ä. No. 165-163 (decomposition) F F -No. r v nOK ^ OCH ^ CH  -No. 135 (decomposition) (Z) n C ₄ H 90 CH = CK-  No, 170 (decomposition) (E) (CH ₃ ) ₃ Si (CH ₃ ) ₃ - No, ^CH 3 ° - ^> - No, 177 (decomposition) No, crystals h ₃ c Ho-Zy -N (CH ₃ ) ₂ h ₃ c ^z -C ₄ H ₉ NHCHj

198

Bile. R

no.

Physical data (melting point in ° C)

4. 123 L-Cj ktx) -N (CK ₃ ) ₂ 4. L 24 I-CIK; -nhnh ₂ 4. L 25 QH-C ,, -N (CK ₃ ) ₂ 4126 QH-C ,, ₂ 4,127 ^C QQ: -NH-M = CK-C ₃ H- 4,123 QH-C ,, -NH-OH 4.129 QH-C ,, -NH-nC ₃ H ₇ 4,130 C-C-L: -FROM \ CCH. 4131 Br- (CH ₂ ) ₅ - -nh ₂ 4.132 KCK -) .- -νή ₂ 4.133 C (c - _{2) 5} - -ΝΉ ₂ 4.134 NsCSCCK-JS- -nh ₂ 4.135 CK.COOCG _LJs--NH2 4,136 <QS ^ _{(CH2) 5} - ₂ .níh 4137 cW (CH9 ₅ -nh ₂ 4.133 n ₃ - (Ch ₂ ) ₄ - -nh ₂ 4139 c-QE - CH ₂ - -ne ₂ 4.140 CK ₂ = CH- (CK ₂₎ 2- -NK ₂ C'C-Hg UL- -nh ₂ 4.141 1 S- (CH ₂ ) ₄ - 4.142 NaO ^ CH - -NK ₂ CK ₂ -8y 4.143 C'HSr - (CH ₂ ) ₇ . -nh ₂ 4.144 HS- (CH ₂ ) ₄ - -nh ₂ 4,145 h ₂ NCH ₂ S (CH ₂ ) ₄ -NH ₂

OCH

4.146. CH ₃ CH-IC ₃ H ₇

-nh ₂

199

Bile.

No.

R ¹

Physical data (melting point in ° C)

4.147

4.148

4,149

4.150

4.151

4.152

4.153

4.154

4155

4.156

4,157

4.158

4.159

4.160 iC ₃ H ₇ NH (CH, J _d -NH, h ₃ C

108 (decomposition)

165 (decomposition)

c-c -nhoc ₂ h ₅ OCOH -NHOH CH, 1 ^J 1 nC ₃ H ₇ -Si - (CH ₂ ) ₃ - -nh ₂ (! h ₃ Br-CH, - -nh ₂ c-Cohu -NH-C (CH ₃ ) ₂ -OCH C-CH, - NH, I-CH, - -nh ₂ ^c -C 6 H _n -NH-CH ₃

crystals

200

Bile.

no.

/

-O 3

Physical data (melting point in ° C)

4.161

4.162

4163

4.164

4.165 4.ióó

4.167

4,168

4169

4.170 ch ₂ = ck ^c 'QHii cC ₅ H ,, cC ₆ H _n cC ₆ H ,, (CH ₂ ) ₃ CH (CH ₂ ) ₂ (E) -I-C, H90-CH = CH (ZVi-C ^ OC ^ CK-nh ₂

CCCH

-NH · '- (CH. ^ - NHCCCfC-C ^

H

The

-nh- <ck ₂ \ ——> ccch

NHCCC (- C -i.}

-NK-CCK--COOE resin

-NH- (CH 2) ₅ -COO ^e Na ^S 150 (decomposition)

-NH ₂

-nh ₂

-nh ₂

NH,

NH,

4171

4172

4173

4.174

4.175

4.176

4177

4.178

4.179

4,180

N ₃ - (CH ₂ ) ₅ (E) -C ₂ H _with O-CH = CH (Z) -C ₂ H ₅ O-CH = CH (Z) -C ₂ H ₅ O-CH = C (CH ₃ ) ch ₂ = ch-ch ₂ ch ₃ -ch = ch ⁿ 'CgH17-ΝΉ,

-nh ₂

-nh ₂

-nh ₂

-nh ₂

-nh ₂ . -nh ₂ -nh ₂ -nh ₂

-NH- (CH 2) ₆ -NHCO ₂ -tC ₄ H 9 crystals crystals

201

Bile. R ¹

no.

Physical data (melting point in ° C)

-NH ₂ crystals crystals crystals crystals

142-145

147-149

133-135

117-119

I6ó (decomposition)

202

Examples of formulations of the active compounds of the formula I (the percentages given are percentages by weight)

Example F1

Emulsion concentrates of the active substance according to the table calcium dodecylbenzenesulphonate castor oil polyglycol ether (36 moles of ethylene oxide) octylphenol polyglycol ether (7-8 moles of ethylene oxide) cyclohexanone mixture of aromatic hydrocarbons containing 9-12 carbon atoms

a)%

%%

%

(b)% 8%%

C)% 6%

%%

(d)% 8%%

% 20%%

An emulsion of any desired concentration can be prepared from such concentrates by dilution with water.

Example F2

solutions

a) b) c) d) active substances according to the table 5% 10% 50% 90% dipropylene glycol methyl ether - 20% 20% - polyethylene glycol with molecular weight weight 400 20% 10% - - N-methyl-2-pyrrolidone - - 30% 10% mixture of aromatic hydrocarbons containing 9-12 atoms carbon 75% 60% - -

The solutions are suitable for use as microdroplets

203

3i E »''

Example F3

Wettable powders Active substances according to the table

% 4% 2%% 88%

b)%

% 3%%

(c)% 3%%

% 5%%

d)%

% 6%%

The active ingredient is thoroughly mixed with the additives and the mixture is ground well in a suitable mill. A wettable powder is obtained which can be diluted with water to suspensions of any concentration.

Example F4

Coated granules

The active substances according to the table are highly dispersed silicon dioxide inorganic carrier (mean

0.1 - 1 mm), for example calcium carbonate or silica

a)

0.1% 0.9%

b)% 2%

c)% 2%

99.0% 93% 83%

The active substance is dissolved in methylene chloride, the solution is sprayed onto the carrier and the solvent is then evaporated off under vacuum.

204

Example F5

Coated granules of the active ingredient according to the table polyethylene glycol with a molecular weight of 200 high disperse silica inorganic carrier (diameter

0.1 - 1 mm), for example calcium carbonate or silica

a) b) c) 0.1 % 5% 15% 1.0 % 2% 3% 0.9 % 1% 2%

98.0% 92% 80%

The finely divided active substance is uniformly applied to a carrier material moistened with polyethylene glycol in a mixer. Non-dusted coated granules are thus obtained.

Example F6

Extruded granules of the active ingredient according to the table sodium lignosulfonate carboxymethylcellulose kaolin

a) b) c)

0.1% 3% 5%

1.5% 2% 3%

1.4% 2% 2%

97.0% 93% 90%

d)% 4% 2%

The active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and finally dried in a stream of air.

I

205

Example F7

dusts

a) b) c) active substances according to the table 0.1% 1% 5% talc 39.9% 49% 35% kaolin 60.0% 50% 60%

By mixing the active ingredient with the carriers and grinding the mixture in a suitable mill, dusts suitable for immediate use are obtained.

Example F8

Suspension concentrates

a) b) c) d) active substances according to the table 3% 10% 25% 50% ethylene glycol 5% 5% 5% 5% nonylphenolpolyglycolether (15 mol ethylene oxide) - 1% 2% - sodium lignosulfonate 3% 3% 4% 5% carboxymethylcellulose 1% 1% 1% 1% 37% aqueous formaldehyde solution 0.2% 0.2% 0.2% 0.2% silicone oil emulsion 0.8% 0.8% 0.8% 0.8% Water 87% 79% 62 38%

The finely divided active ingredient is thoroughly mixed with the additives. This gives a suspension concentrate from which suspensions of the desired concentration can be prepared by dilution with water.

206

Biological examples

Example B1

Herbicidal action before emergence of plants

The monocotyledonous and dicotyledonous test plants are sown in standard soil in plastic containers. Immediately after sowing, test substances are sprayed (in 500 l of water per hectare) in the form of an aqueous suspension (prepared from the formulation of Example F1) at a dose corresponding to 2 kg of active substance per hectare. The test plants are then grown in a greenhouse under optimal conditions. After a test period of 3 weeks, the experiment is evaluated using a nine-step spanner (1 = complete damage, 9 = no effect). Results 1 to 4 (especially 1 to 3) indicate good to very good herbicidal action.

Table Bl

Preemergence

test plant Aven Setaria Sinaois Steiiaria active substance no. 1,015 1 2 1 1 1016 I 1 5 X and 1,018 1 2 1 3 1,019 1 1 1 1 1,021 1 4 1 1 1,039 1 2 9 3 1.060 3 3 3 and 1,075 2 1 1 1

207

Table BI continuation

test plant effective love no. Avena Setaria sinapis Stellaria 1,075 ABOUT 4th 2 4 3 i. 07 S 3 1 1 1 1.079 3 1 4 1 1,081 2 2 3 and 1.10S 2 1 6 4 1.112 2 1 3 1.113 2 2 3 1 1 191 4 2 1 1 93 1 93 1 1 1 1 1.124 £ 1 1 1 1,125 and 2 1 1 1,127 2 1 1 1 1.140 2 n 4th 1 1 1 1 41 1 1 1 and 1,150 2 3 5 1 1151 1 1 1 1 1,191 1 1 3 1 1,235 2 2 1 1 1,237 1 1 1 1 1,240 2 2 1 1 1241 1 4 1 1 1.259 2 1 1 9 1,278 2 2 3 5 1.282 6 3 1 3 1293 2 4 4 2

208

The same results are obtained when the compounds of formula I are formulated according to suitable examples F2-F8.

Example B2

Post-emergence herbicidal action

The monocotyledon and dicotyledon test plants are grown in standard greenhouse soil in plastic containers and sprayed at 4-6 leaf stage with an aqueous suspension of test compounds of Formula I prepared from 25% wettable powder (Example F3, b)) at a dose corresponding to 2000 g of active substance per hectare (in 500 l of water per hectare). The test plants are then grown in a greenhouse under optimal conditions. After a test period of approximately 18 days, the experiment is evaluated using a nine-step spanner (1 = complete damage, 9 = no effect). Results 1 to 4 (especially 1 to 3) indicate good to very good herbicidal action. In this experiment, the compounds of formula I exhibit a strong herbicidal action. The same results are obtained when the compounds of formula I are formulated according to Examples F1 to F2 and F4 to F8.

209

Table B2

Postemergence

test plant Setaria sinapis Stsllaria active substance no. 1,237 - 5 1 1,141 7 2 1 1 " 1,075 * 2 1 1 1,137 5 1 2 1,021 1 3 T_ 1_

The same results are obtained when the compounds of formula I are formulated according to suitable examples F2 to F8.

Claims (22)

PATENT CLAIMS 1. 1,2,4,6-Thiatriazines of the formula I NR ² F? C 1 -C 20 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl and C 1 -C 17 -alkyl, C 1 -C 17 -alkylcycloalkyl C 3 -C 8 alkyl, C 2 -C 17 alkenyl, C 3 -C 8 cycloalkylalkenyl C 2 -C 17 alkenyl, C 2 -C 17 alkenylcycloalkyl C 3 -C 8 alkenyl and C 3 -C 8 alkynyl, alkynyl carbon atoms, cycloalkylalkynyl C 2 -C 17 alkynyl, C 2 -C 17 alkynyl cycloalkyl and C 3 -C 8 alkynyl carbon atoms in the cycloalkyl moiety, a cycloalkenyl group of 5 to 5 carbon atoms; (C,-Clo) cycloalkenylalkyl having 5 to 8 carbon atoms in the cycloalkenyl moiety and 1 to 17 carbon atoms in the alkyl moiety, an alkylcycloalkenyl group having 1 to 17 carbon atoms in the alkyl moiety and 5 to 8 carbon atoms having a 2 to 17 carbon atoms in the 3 to 17 carbon atoms 8 211 ka in the cycloalkenyl moiety, a cycloalkenylalkenyl group having 5 to 8 carbon atoms in the cycloalkenyl moiety and 2 to 17 carbon atoms in the alkenyl moiety, an alkenylcycloalkenyl group having 2 to 17 carbon atoms in the alkenyl moiety and 5 to 8 carbon atoms in the cycloalkenyl alkenyl moiety, cycloalkenyl (C 5 -C 8) cycloalkenyl and (C 2 -C 17) alkynyl group, (C 2 -C 17) alkynylcycloalkenyl (C 5 -C 8) cycloalkenyl, (C 3 -C 8) cycloalkylcycloalkyl group each cycloalkyl, cycloalkenylcycloalkenyl of 5 to 8 carbon atoms in each cycloalkenyl portion, cycloalkylcycloalkenyl of 3 to 8 carbon atoms in the cycloalkyl portion and 5 to 8 carbon atoms in the cycloalkenyl portion, cycloalkenylcycloalkyl of the 5 to 8 carbon atom; 3 a - C 8 cycloalkyl, C 2 -C 17 alkynylalkenyl and C 2 -C 17 alkenyl, or C 2 -C 17 alkenyl and C 2 -C 17 alkynyl, these groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo, -OR ³ , -S (O) _n R ⁶ , -COOR ⁷ , -CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ¹² , = N-NR ^X3 R ^X4 , phenyl, biphenyl, naphthyl or heterocyclyl, wherein the phenyl, naphthyl and heterocyclyl substituents may be unsubstituted or substituted by halogen, cyano, nitro, -OR ³ , -NR ^XO R ^XX or -CONR ⁸ R ⁹ , or R ¹ represents a heterocyclyl group, the heterocycle being attached to the thiatriazine ring through one of its carbon atoms and wherein the heterocycle may be substituted by halogen, cyano, nitro, oxo, -OR ³ , -S (O) _n R ®, - COOR ⁷ , 212 -CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ^{X 2} , = N-NR ^{X 3} R ^{X 4} , C 1 -C 17 alkyl, C 2 -C 17 alkenyl, C 2 -C 17 alkynyl , cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 5-8 carbon atoms, phenyl, biphenyl, naphthyl, alkyl of 1 to 17 carbon atoms, which is substituted by halogen, cyano, nitro, a group ^of -0R , -CONR ^e R ⁹ or -NR ^XO R ^XX , a C 2 -C 17 alkenyl group substituted with halogen, cyano, nitro, -OR ^S , -CONR ^and R ⁹ or -NR ^XO R ^XX , alkynyl C 2 -C 17 substituted by halogen, cyano, nitro, -OR ^S , -CONR ^and R ⁹ or -NR ^XO R ^XX , C 3 -C 8 cycloalkyl substituted by halogen, cyano, nitro , -0R ^p , -CONR ⁹ R ^S, or -NR R ^{XO XX,} cycloalkenyl having 5 to 8 carbon atoms which is substituted by halogen, cyano, nitro, -OR ^5, -CONR ⁹ R ^S, or -NR R ^{XO XX,} phenyl which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, biphenyl which is substituted by halogen, cyano, nitro, -OR ^5, -CONR ^a R ^9, or -NR R ^{XO XX} or naphthyl which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR R ^{XO XX,} or R ^x represents phenyl, biphenyl, naphthyl, C 1 -C 10 alkylphenyl, C 1 -C 10 alkylbiphenyl, C 1 -C 10 alkylnaphthyl, alkenylphenyl (C 2 -C 10) alkenyl, (C 2 -C 10) alkenylbiphenyl, (C 2 -C 10) alkenyl naphthyl (C 2 -C 10) alkenyl, 213 alkynylphenyl of 2 to 10 carbon atoms in the alkynyl moiety, alkynylbiphenyl of 2 to 10 carbon atoms in the alkynyl moiety or alkynyl naphthyl of 2 to 10 carbon atoms in the alkynyl moiety, which may be unsubstituted or substituted by halogen, cyano, nitro , -0R ^the group -S (O) _n R ^e, -COOR ^7, -CONR ^a R® or -NR ^XO R ^L1, wherein R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 7 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino carbon, -N = CH ₂ , -N = CH-alkyl of 1 to 4 carbon atoms in the alkyl moiety, -N = C (alkyl) ₂ of 1 to 4 carbon atoms in each alkyl moiety, trialkylsilyl of 3 up to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 7 carbon atoms or alkynyl of 3 to 7 carbon atoms, n is 0 , 1 or 2 R ⁶ represents a hydrogen atom or a cyano group when n is 0, or R ⁶ represents an alkyl group having 1 to 5 carbon atoms, a haloalkyl group. (C 1 -C 5) alkyl, (C 1 -C 5) hydroxyalkyl, phenyl, naphthyl, (C 1 -C 4) alkylphenyl, (C 1 -C 4) alkylnaphthyl, halo214 (phenyl), halogen (naphthyl) a heterocyclyl group, a haloocyclyl group or a C 3 -C 7 cycloalkyl group, R ⁷ is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 6 nitroalkyl, C 1 -C 6 cyanoalkyl, phenyl, naphthyl, halophenyl , halo-phenyl, C 2 -C 10 alkoxyalkyl, C 1 -C 10 alkylcarbonyl, heterocyclyl, halo-heterocyclyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halo-cycloalkyl-N, CH _2, N = CH-C 1 -C 4 alkyl, a group -N = C _{(alkyl), and} C 1 -C 4 alkylamino or dialkylamino having 2 to 6 carbon atoms; R ® and R ® are each independently hydrogen, phenyl, naphthyl, halophenyl, halophthyl, alkyl with from 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, phenoxy, naphthoxy, halo-phenoxy, halo-phenoxy, cyanoalkyl of 1 to 7 carbon atoms, alkenyl 3 alkynyl of 3 to 7 carbon atoms or alkoxyalkyl having 2 to 8 carbon atoms and the symbols ^R and R® together with the nitrogen to which they are attached form heterocycle, which may be halogenated; R ¹⁰ and R each independently ^xx they are in each case hydrogen, phenyl, naphthyl, halophenyl, halophthyl, alkyl 215 of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, phenoxy, naphthoxy, halo-phenoxy, halo-phenoxy, cyanoalkyl of 1 to 7 carbon atoms, alkenyl 3 , (C 3 -C 7) alkynyl, (C 2 -C 8) alkoxyalkyl, (C 1 -C 6) alkylamino, (C 2 -C 6) dialkylamino, formyl, (C 2 -C 8) alkylcarbonyl, phenylcarbonyl, or naphthylcarbonyl, wherein the phenyl or naphthyl radical in these groups may be substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, hydroxy, cyano, nitro or C 1 -C 6 alkoxy, or by symbols R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are present linked, form a heterocycle which may be halogenated, R ¹² represents a hydrogen atom, a C 1 -C 8 alkyl group, a C 1 -C 8 haloalkyl group, a phenyl group, a halophenyl group, a cyanophenyl group, a nitrophenyl group, a C 1 -C 4 alkylphenyl group, an alkoxyphenyl group C 1 -C 4 alkoxy, naphthyl, cyanonaphthyl, nitronaphthyl, halogenaphthyl, C 1 -C 4 alkylnaphthyl, C 1 -C 4 alkoxynaphthyl, phenylalkyl C6 alkyl or naphthyl-to 6 carbon atoms in the alkyl moiety, and the radicals R ¹³ and R ³ - ^-4, independently of one another are hydrogen, alkyl having 1 to 6 carbon atoms, alkylkar216 diradical of 1 up to 6 carbon atoms, phenyl, halophenyl, cyanophenyl; Upin, nitrophenyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkoxyphenyl, naphthyl, cyanonaphthyl, nitronaphthyl, halogenaphthyl, C 1 -C 4 alkylnaphthyl alkyl or C1 -C4 alkoxy naphthyl, R @ ² and R @ ^{3 are} each independently hydrogen, C1 -C6 alkyl, C1 -C6 alkyl which is substituted halogen, cyano, nitro, C 1 -C 8 alkoxy, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium, carboxy, -COOM, wherein M represents an ammonium group or an alkali metal atom or atom alkaline earth metal, C 3 -C 8 cycloalkyl, C 1 -C 5 alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C 1 -C 6 alkylamino, C 1 -C 5 alkoxycarbonyl, C 2 -C 12 dialkylamino phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, bifenyloxyskupinou, phenylthio or naphthylthio, the above-mentioned aromatic ring may be unsubstituted or substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{1 O 1: L,} alkyl (C 1 -C 4), formyl, (C 1 -C 4) alkylcarbonyl, COOR · ⁷ , (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfonyl or CONR ^e R ⁽ R) group, or R ² and R ^{3 are} each independently C 2 -C 6 alkenyl, C 2 -C 6 alkenyl substituted with halogen, cyano, nitro, C 1 -C 8 alkoxy, trialkylsilyl (C 3 -C 6), hydroxy, amino, ammonium, (C 1 -C 4) trialkylammonium, carboxyl, -COOM, where M is an ammonium or alkali metal or alkaline earth metal atom, or cycloalkyl C 3 -C 8 alkyl, C 2 -C 5 alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C 1 -C 6 alkylamino, C 2 -C 5 alkoxycarbonyl, C 2 -C 12 naphthyl dialkylamino, phenyl , phenoxy, naphthoxy, biphenyl s Kupino, bifenyloxyskupinou, phenylthio or naphthylthio, the above-mentioned aromatic rings may be unsubstituted or substituted by halogen, cyano, nitro, -0R ^a, -NR ^XX R ^XO, alkyl of 1 to 4 carbon atoms, a formyl group, an alkylcarbonyl group with (C 1 -C 4), COOR ⁷ , (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfonyl, or CONR ^S R ®, or R ² and R ^{3 are} each independently C 3 -C 4 alkynyl. C 6 -C 6 alkynyl substituted with halogen, cyano, nitro, C 1 -C 8 alkoxy, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium, 1-trialkylammonium up to 4 carbon atoms in each alkyl moiety, carboxyl group, -COOM group wherein M is an ammonium group or an alkali metal or alkaline earth metal atom, or a C 3 -C 8 cycloalkyl group, a C 1 -C 5 alkylcarbonyloxy group, a phenylcarbonyloxy group, a naphthylcarbonyloxy group, a C 1 -C 6 alkylamino group, (C 1 -C 5) dialkyl, (C 2 -C 12) dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenylthio or naphthylthio group, wherein the above aromatic rings may be unsubstituted or substituted by halogen, cyano, nitro -0R ^p, NR ⁱ R ^lo -, alkyl having 1 to 4 carbon atoms, a formyl group, an alkylcarbonyl group having 1 to 4 carbon atoms, COOR ⁷ ·, alkylthio having 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon or sku Pina CONR ^with R®, and the symbols R ² and R ³ independently of one another are formyl, alkylcarbonyl -C 15 carbon atoms, an alkenylcarbonyl group having 2 to 15 carbon atoms, cycloalkylcarbonyl having 4 to 9 carbon atoms, a cycloalkenylcarbonyl group, (C až-C 9) or cycloalkylalkylcarbonyl of (C 8-C 8) cycloalkyl and (C až-C alky) alkyl groups, which groups may be substituted by halogen, cyano, nitro, hydroxy, amino, (C 1 -C 6) alkylamino , C 2 -C 12 dialkylamino, carboxyl, -COOM, where M is an ammonium or alkali metal or alkaline earth metal atom, or a C 1 -C 8 alkoxycarbonyl group, a C 4 -C 10 cycloalkoxycarbonyl group , an alkylaminocarbonyl group having from 1 to 8; carbon atoms or a C 2 -C 12 dialkylaminocarbonyl group; or R @ ² and R @ ^{3 are} each independently heterocyclyl, heterocyclylcarbonyl, heterocyclyl substituted by halogen, cyano, nitro, C1 -C5 alkyl, C1 -C5 alkoxy, C1 -C5 alkylcarbonyl; (C 1 -C 5) alkyl, (C 1 -C 5) alkylcarbonyloxy, (C 1 -C 6) alkoxycarbonyl, aminocarbonyl, (C 1 -C 6) alkylaminocarbonyl or (C 2 -C 11) alkylaminocarbonyl, or heterocyclylcarbonyl group which is substituted with halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, aminocarbonyl, C 1 -C 6 alkylamino Uhl The radicals R @ ² and R @ ³ independently of one another are phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenylalkylcarbonyl having 1 to 6 carbon atoms in the alkyl part, biphenylcarbonyl having 1 to 6 carbon atoms. C 1 -C 6 naphthylalkylcarbonyl, C 2 -C 6 phenylalkenylcarbonyl, C 2 -C 6 biphenylalkenylcarbonyl, C 2 -C 6 naphthylalkenylcarbonyl alkenyl, C3 -C6 phenylalkynylcarbonyl, C3 -C6 biphenylalkynylcarbonyl, or C3 -C6 naphthylalkynylcarbonyl, the alkynylcarbonyl moiety may be selected from the group consisting of: substituted with an alkyl group of 1 to 5 220 carbon atoms, C 1 -C 5 alkoxy, C 1 -C 5 alkylthio, C 1 -C 5 haloalkyl, C 1 -C 5 alkylcarbonyl, halogen, cyano, amino, nitro, —COOR ⁷ , (C 1 -C 8) alkoxycarbonyl, hydroxy, (C 1 -C 5) alkylsulfinyl, (C 1 -C 5) alkylsulfonyl, (C 1 -C 6) alkylaminocarbonyl or (C 2 -C 12) dialkylaminocarbonyl, or symbols R ² and R ^{3 are} each independently phenyl, naphthyl or heterocyclyl, which may be substituted by halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylthio 1 to 5 carbon atoms, carboxyl, - C ₀ NH ₂ , C 1 -C 6 alkylaminocarbonyl, C 2 -C 10 dialkylaminocarbonyl, C 1 -C 5 alkylcarbonyl or C 1 -C 5 alkoxycarbonyl, or R ² and R ³ together with the nitrogen atom to which they are attached form a heterocyclic ring which may be substituted by alkyl having 1 to 5 carbon atoms, alkoxy of 1-5 carbon atoms, halogen, cyano or nitro, or the radicals R ² and R ³ independently of one another are amino, , (C 1 -C 6) alkylamino, (C 2 -C 8) dialkylamino, phenylamino, naphthylamino, (C 1 -C 6) alkylcarbonylamino, (C 1 -C 10) alkoxycarbonylamino (C 1 -C 6) alkoxy, (C 1 -C 6) alkoxy until 221 6 carbon atoms, phenoxy, biphenyloxy or naphthoxy, X is O or S (O) _x , wherein x is 0, 1 or 2, and R ⁴ represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkynyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 5 to 8 carbon atoms, a cycloalkylalkyl group C 3 -C 8 cycloalkyl and C 1 -C 4 alkyl or C 1 -C 4 alkylcycloalkyl C 3 -C 8 cycloalkyl, which groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo or ^a group -0R, or R ⁴ represents a phenyl group, a biphenyl group, a naphthyl group, a heterocyclyl group, an alkylphenyl group having 1 to 4 carbon atoms in the alkyl moiety, an alkylnaphthyl group having 1 to 4 carbon atoms in the alkyl moiety, a phenylalkyl group having 1 to 4 carbon atoms in the alkyl moiety or a (C 1 -C 4) naphthylalkyl group, which groups may be unsubstituted or substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy , (C 1 -C 6) alkylamino, (C 2 -C 8) dialkylamino, (C 1 -C 10) alkylthio, (C 1 -C 10) haloalkyl, (C 1 -C 10) haloalkoxy (C 1 -C 10) haloalkylthio, C 2 -C 10 alkoxycarbonylalkoxy alkylsulfinyl C 1 -C 6, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkyloxycarbonyl, C 1 -C 6 alkylcarbonyl, -CONH ₂ , formyl, C 1 -C 7 alkylaminocarbonyl carbon, C 2 -C 11 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl, C 1 -C 10 alkylcarbonylamino, C 1 -C 10 alkylcarbonyloxy, phenoxy, halo-phenoxy, alkynyl, pyridyloxy or pyridyloxy; (C 1 -C 4), (C 1 -C 4) alkoxy, cyano, nitro or amino, or two adjacent substituents on the phenyl or naphthyl ring R ⁴ form a carbocyclic or heterocyclic ring which may be substituted by halogen, cyano, nitro, amino carboxy, oxo, C 1 -C 10 alkyl, C 1 -C 10 alkyloxy, C 1 -C 10 alkylthio, C 1 -C 10 haloalkyl, hydroxy, C 3 -C 10 alkoxycarbonylalkoxy , (1-6C) alkylsulfinyl, (1-6C) alkylsulfonyl, (2-6C) alkoxycarbonyl, (2-6C) alkylcarbonyl, -CONH ₂ , formyl, (2-6C) alkylaminocarbonyl C 7 -C 3 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl, C 2 -C 10 alkylcarbonylamino, C 2 -C 10 alkylcarbonyloxy, phenoxy, pyridyloxy or pyridyloxy group; C 1-4 alkyl ka, C 1 -C 4 alkyl, cyano, nitro or amino, 223 and the salts of 1,2,4,6-thiatriazine of the formula I, with the exception of 1,2,4,6-thiatriazine of formulas I, Ia, Ia _{iZ 2,} Ia ₃ and Ia NH, N W // \ CH, CH, - S N 3 of \ / N = < NH, N w //, _T 1 H ₃ Cs N ^(Ia) 'V 0 ^and i) · S-CH ₃ nh ₂ ^N w / nC _d Ho-SN O-phenyl nh ₂ 'v // (Ia ₂ ), CI (CH ₂ ) ₄ -SN (Ia ₃ ) and N ^: O-phenyl O-phenyl NH, ^N w // H _{3 EN} N (Ia ₄ ) o-ch ₃ The 1,2,4,6-thiatriazines of formula I according to claim 1, wherein: R ¹ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkylalkyl group having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl moiety, an alkylcycloalkyl group having 1 to 8 carbon atoms C 3 -C 8 alkyl, C 2 -C 10 alkenyl, C 3 -C 8 cycloalkyl C 2 -C 6 alkenyl, C 2 -C 8 alkenylcycloalkyl C 3 -C 8 alkenyl, C 2 -C 10 alkynyl, cycloalkylalkynyl C 3 -C 8 cycloalkyl and C 2 -C 6 alkynyl, C 2 -C 8 alkynylcycloalkyl C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, cycloalkenylalkyl of 5 to 8 carbon atoms in the cycloalkenyl moiety of 1 to 6 carbon atoms in the alkyl moiety, alkylcycloalkenyl of 1 to 8 carbon atoms in the alkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylalkenyl of 5 to 8 carbon atoms in the cycloalkenyl having 2 to 6 carbon atoms in the alkenyl moiety, alkenylcycloalkenyl having 2 to 8 carbon atoms in the alkenyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylalkynyl having 5 to 8 carbon atoms in the cycloalkenyl moiety and 2 to 6 carbon atoms in the alkynyl moiety, an alkynylcycloalkenyl group having 2 to 8 carbon atoms C 5 -C 8 alkynyl, C 5 -C 8 cycloalkylcycloalkyl, C 3 -C 8 cycloalkylcycloalkyl, C 5 -C 8 cycloalkenylcycloalkenyl, C 3 -C 8 cycloalkylcycloalkenyl C 5 -C 8 cycloalkenyl, C 5 -C 8 cycloalkenyl C 3 -C 8 cycloalkenyl, C 2 -C 8 alkynylalkenyl, C 2 -C 6 alkynyl alkenylcarbonyl or alkenylalkinylovú having 2 to 8 carbon atoms in the alkenyl moiety and from 2 to 6 carbon atoms in the alkynyl part, which groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo, -0R ^the group, -S (O R _n , -COOR ⁷ , -CONR ^and R ⁹ , -NR ^XO R ^XX , = NR ^{X 2,} phenyl, biphenyl, naphthyl or heterocyclyl, said phenyl, naphthyl and heterocyclyl substituents may be substituted by NE225 or substituted by halogen, cyano, nitro, -0R ^a, -NR a R ^{XO XX} or CONR ^and R ⁹ , or R ^x represents a heterocyclyl group, wherein the heterocycle is attached to the thiatriazine ring through one of its carbon atoms and wherein the heterocycle may be substituted by halogen, cyano, nitro, oxo, -OR ⁵ , -S (O) _n R ⁶ , - COOR ⁷ , -CONR ® R ®, -NR ^XO R ^XX , = NR ^{X 2} , = N-NR ^{X 3} R ^{X 4} , C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl C 8 -C 8 cycloalkyl, C 8 -C 8 cycloalkenyl, phenyl, biphenyl, naphthyl, C 1 -C 8 alkyl substituted with halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR ^XX R ^XO, alkenyl of 2 to 8 carbon atoms, which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ⁸ R ⁹ or -NR R ^{XO XX} , alkynyl group a 2-8 carbon atom substituted with halogen, cyano, nitro, -OR ⁵ , -CONR ^and R ⁹ or -NR ^XO R ^XX , a 3-8 cycloalkyl substituted with halogen, cyano, nitro, -OR ⁵ , -CONR ^and R ⁹ or -NR ^XO R ^XX , C 5 -C 8 cycloalkenyl substituted with halogen, cyano, nitro, -OR ⁵ , -CONR ^and R ⁹ or -NR ^X ° R ^XX , phenyl substituted with halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, -OR ⁵ , -CONR ^S R ®, or -NR ^XO R ^XX, biphenyl which is substituted by halogen, cyano, nitro, -0R ^a, -CONR ^a R ⁹ or -NR R ^{XO XX} or naphthyl which is substituted by halogen, cyano, nitro, -OR ^5, 226 -CONR ^and R ⁹ , or -NR ^XO R ^XX or R ^x represents phenyl, biphenyl, naphthyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylbiphenyl, C 1 -C 4 alkylnaphthyl, alkenylphenyl (C 2 -C 4) alkenyl, (C 2 -C 4) alkenylbiphenyl, (C 2 -C 4) alkenylnaphthyl, (C 2 -C 4) alkynylphenyl, (C 2 -C 4) alkynylbiphenyl -C 4 -alkynyl or alkinylnaftylovú having 2 to 4 carbon atoms in the alkynyl part, which groups may be substituted by halogen, cyano, nitro, -0R ^p, s (O) _n R ^e, -COOR ^7, -CONR ^and R ® or -NR ^XO R ^XX , wherein R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 4 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms or an alkynyl group having 3 to 4 carbon atoms, n being 0, 1 or 2 227 R ⁶ represents a hydrogen atom or a cyano group when n is 0, or R ⁶ is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl, C 1 -C 4 alkylphenyl, halogenphenyl, heterocyclyl, halo-heterocyclyl or cycloalkyl; 6 carbon atoms, R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, R® and R ⁹ are each independently hydrogen, phenyl, halophenyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl; , a (C až-C alk) alkenyl group, a (C až-C alk) alkynyl group or a (C R-C®) alkoxyalkyl group, or R® and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may: be halogenated; R ¹⁰ and R ¹¹ independently of one another are hydrogen, phenyl, halophenacyl a C1-4 alkyl group, a C1-4 haloalkyl group, a C1-4 cyanoalkyl group, a C3-4 alkenyl group, a C3-4 alkynyl group, an alkoxyalkyl group C 2 -C 4 -alkyl, formyl, C 1 -C 4 -alkylcarbonyl or phenylcarbonyl, the phenyl The 228 radical in these groups may be substituted by a C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, hydroxy, cyano, nitro or C 1 -C 4 alkoxycarbonyl group, or R ^xo and R ¹¹ together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated, and R ¹² represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a phenyl group, a halogenophenyl group, a cyanophenyl group, a nitrophenyl group, an alkylphenyl group having 1 to 4 carbon atoms in the alkyl moiety, an alkoxyphenyl group C 1 -C 4 alkoxy or C 1 -C 4 phenylalkyl. The 1,2,4,6-thiatriazines of formula I according to claim 1 2, in which R ^x is C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkylalkyl and C 1 -C 6 alkyl, C 1 -C 8 alkylcycloalkyl C 3 -C 8 alkyl, C 2 -C 10 alkenyl, C 3 -C 8 cycloalkyl C 2 -C 6 alkenyl, C 2 -C 8 alkenylcycloalkyl C 3 -C 8 alkenyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkylalkynyl C 2 -C 6 alkynyl, C 2 -C 8 alkynylcycloalkyl 22 8 carbon atoms in the alkynyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, cycloalkene C 5 -C 8 -alkyl, C 5 -C 8 -cycloalkenylalkyl having 1 to 6 carbon atoms in the alkyl moiety, C 1 -C 8 alkylcycloalkenyl and 5 to 8 carbon atoms in the cycloalkenyl moiety a (C 5 -C 8) cycloalkenylalkenyl group having 2 to 6 carbon atoms in the alkenyl moiety, an C 2 -C 8 alkenylcycloalkenyl group having 5 to 8 carbon atoms in the cycloalkenyl moiety, and a C 5 -C 8 cycloalkenylalkinyl group carbon atoms in the cycloalkenyl moiety and 2 to 6 carbon atoms in the alkynyl moiety, alkynylcycloalkenyl having 2 to 8 carbon atoms in the alkynyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkylcycloalkyl of 3 to 8 carbon atoms in each cycloalkyl phenyl moiety, C 5 -C 8 in each cycloalkenyl moiety, a cycloalkylcycloalkenyl group of 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, a cycloalkenylcycloalkyl group of 5 to 8 carbon atoms in the cycloalkenyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety; C 2 -C 8 alkynyl and C 2 -C 6 alkenyl or C 2 -C 8 alkenylalkynyl and C 2 -C 6 alkynyl, which groups may be unsubstituted or substituted by halogen, cyano , oxo, -0R ^p, -COOR ^7, -CONR ^e R ^9, -NR ^XX R ^XO or phenyl, wherein the phenyl ring may be unsubstituted or substituted with halogen, or R ^x represents a heterocyclyl group, the heterocycle being attached to the thiatriazine ring via one of 230 carbon atoms thereof, and wherein the heterocycle may be substituted by halogen, cyano, oxo, -0R ^the group -S (O) _n R ^a, -COOR ^7, -CONR ^with R ^9, -NR ^XX R ^XO, alkyl p C 1 -C 8 alkenyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, phenyl, C 1 -C 8 alkyl 8 C atoms which is substituted by halogen, cyano, -0R ^a, -CONR R® ^s or NR R ^{XO XX,} alkenyl of 2 to 8 carbon atoms, which is substituted by halogen, cyano, -OR ^3, - CONR ^e R ⁹ or -NR ^X R ^XX °, alkynyl group of 2 to 8 carbon atoms, which is substituted by halogen, cyano, -OR ^3, -CONR ^a R ⁹ or -NR ^{X 1} R ^{1 O,} cycloalkyl of 3 to Is substituted by halogen , cyano, -OR ³ , -CONR, ^and R ⁹ or -NR ^XO R ^XX , a C 5 -C 8 cycloalkenyl group substituted with halogen, cyano, -OR ³ , -CONR ^and R ® or -NR ^XO R ( ^XX) or phenyl substituted with halogen, cyano, nitro, (C 1 -C 4) alkyl, (C 1 -C 6) haloalkyl, -OR ³ , -CONR ⁵ R ⁹ or -NR ^XO R ^XX , or R ^x represents phenyl, biphenyl, naphthyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylbiphenyl, C 1 -C 4 alkylnaphthyl, alkenylphenyl (C 2 -C 4) alkenyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkenyl, naphthyl (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynylbiphenyl up to 4 carbon atoms in the alkynyl moiety or alkynyl naphthyl group 231 of 2 to 4 carbon atoms in the alkynyl part, which groups may be unsubstituted or substituted by halogen, cyano, -0R ^p, S (O) _n R ^e, -COOR ^7, -CONR R® ^S or NR ^XO R ^{1: L} , where R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenylalkyl having 1 to 4 carbon atoms C1-4 alkylcarbonyl, benzoyl, halobenzoyl, trialkylsilyl of 3-6 carbon atoms, cycloalkyl of 3-6 carbon atoms, alkenyl of 2-4 carbon atoms or alkynyl of 3 carbon atoms up to 4 carbon atoms, n is 0, 1 or 2, R ⁶ represents a hydrogen atom or a cyano group when n is 0, or R ⁶ is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl or C 1 -C 4 alkylphenyl in the alkyl moiety, R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halogénheterocyklylovú group; R ⁸ and R®, independently of one another are hydrogen, phenyl, halophenyl, alkyl of 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms, cyanoalkyl of 1 232-4 carbon atoms, alkenyl of 3-4 carbon atoms, alkynyl of 3-4 carbon atoms or alkoxyalkyl having 2 to 4 carbon atoms and the symbols ^R and R ³ together with the nitrogen to which they are attached, R @ ¹⁰ and R @ ¹¹ are each independently hydrogen, phenyl, halophenyl, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 haloalkyl; C 4 -C 4 alkenyl, C 3 -C 4 alkenyl, C 4 -C 4 alkynyl, C 2 -C 4 alkoxyalkyl, formyl, C 1 -C 4 alkylcarbonyl or phenylcarbonyl, with a phenyl radical in these groups it may be substituted by a C1-C4 alkyl group, a halogen, a C1-C4 alkoxy group I atoms, hydroxy, cyano, nitro or alkoxycarbonyl group having 1 to 4 carbon atoms, or the radicals R ¹⁰ and R ¹¹ together with the nitrogen to which they are attached form heterocycle, which may be halogenated. 4. The compound according to claim 1 3, in which R ¹ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkylalkyl group having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl moiety, an alkylcycloalkyl group having 1 to 8 carbon atoms C 3 -C 8 -alkyl, C 2 -C 10 -alkenyl, C 3 -C 8 -cycloalkylalkenyl233 k and C 2 -C 6 -alkenyl, C 2 -C 2 -alkenylcycloalkyl C 8 -C 3 alkenyl and C 3 -C 8 cycloalkyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkylalkynyl and C 2 -C 6 alkynyl, C 2 alkynylcycloalkyl up to 8 carbon atoms in the alkynyl moiety and 3 to 8 carbon atoms in the cycloalkyl moiety, cycloalkenes C 5 -C 8 -alkyl, C 5 -C 8 -cycloalkenylalkyl having 1 to 6 carbon atoms in the alkyl moiety, C 1 -C 8 alkylcycloalkenyl and 5 to 8 cycloalkenyl carbon atoms C 5 -C 8 cycloalkenylalkenyl having 2 to 6 carbon atoms in the alkenyl moiety, C 2 -C 8 alkenylcycloalkenyl having 5 to 8 carbon atoms in the cycloalkenyl moiety, C 5 -C 8 cycloalkenylalkinyl moieties 8 carbon atoms in the cycloalkenyl moiety and 2 to 6 carbon atoms in the alkynyl moiety, alkynylcycloalkenyl group having 2 to 8 carbon atoms in the alkynyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, a cycloalkylcycloalkyl group of 3 to 8 carbon atoms in each cycloalkyl moiety cycloalkenylcycloalkenyl of 5 to 8 carbon atoms; each cycloalkenyl, cycloalkylcycloalkenyl of 3 to 8 carbon atoms in the cycloalkyl moiety and 5 to 8 carbon atoms in the cycloalkenyl moiety, cycloalkenylcycloalkyl of 5 to 8 carbon atoms in the cycloalkenyl moiety and 3 to 8 carbon atoms in the cycloalkylalkyl moiety; up to 8 carbon atoms in the alkynyl moiety and 2 to 6 carbon atoms in the alkenyl moiety, or an alkenylalkynyl group having 2 to 8 carbon atoms in the alkenyl moiety and 2 to 6 carbon atoms in the alkynyl moiety, which groups may be unsubstituted or halo substituted; , oxo, -0R ^p, -COOR ^7, -CONR®R ^9, -NR ^XX R ^XO or phenyl, wherein the phenyl ring may be unsubstituted or substituted with halogen, or R ^x represents a heterocyclyl group, the heterocycle being attached to the thiatriazine ring via one of its carbon atoms and wherein the heterocycle may be substituted by halogen, cyano, oxo, C 1 -C 4 alkoxy, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, C 1 -C 8 alkyl substituted with halogen, C 2 -C 8 alkenyl substituted with halogen, alkynyl (C 2 -C 8) group substituted by halogen or phenyl substituted by halogen, cyano, nitro, (C 1 -C 4) alkyl or (C 1 -C 4) alkoxy; or R ^x represents phenyl, biphenyl, naphthyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylbiphenyl, C 1 -C 4 alkylnaphthyl, alkenylphenyl of 2 to 4 carbon atoms in the alkenyl part or alkynylphenyl having 2 to 4 carbon atoms in the alkynyl part, which groups may be unsubstituted or substituted by halogen, cyano, -0R ^p, s (0) ^ R ^6, -COOR ⁷ , CONR ^e R ⁹ or -NR R ^{XO XX:} R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, fenylalky235 fishing having 1 to 4 carbon C1-4 alkylcarbonyl, benzoyl, halobenzoyl, trialkylsilyl of 3-6 carbon atoms, cycloalkyl of 3-6 carbon atoms, alkenyl of 2-4 carbon atoms or alkynyl 3 to 4 carbon atoms, n is 0, 1 or 2, R ⁶ represents a hydrogen atom or a cyano group when n is 0, or R ^A is alkyl of 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms, phenyl or alkylphenyl having 1 -C 4 alkyl, R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, R ^s and R ⁹ are each independently hydrogen, phenyl, halophenyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl; , (C 3 -C 4) alkenyl, (C 4 -C 4) alkynyl or (C 2 -C 4) alkoxyalkyl, or R ^a and R ⁹ together with the nitrogen atom to which they are attached form a heterocycle which may: be halogenated; R ^xo and R ¹¹ independently of one another, are a hydrogen vodí236 ms, phenyl, halogénf C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 1 -C 4 alkynyl (C 2 -C 4), formyl, (C 1 -C 4) alkylcarbonyl or phenylcarbonyl, the phenyl radical of which may be unsubstituted or substituted by (C 1 -C 4) alkyl, halogen, (C 1 -C 4) alkoxy, hydroxy, cyano, nitro or (C 1 -C 4) alkoxycarbonyl, or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated. The compound of formula I according to claim 1 1, wherein R ² and R ^{3 are} each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by halogen, cyano, nitro, C 1 -C 4 alkoxy carbon atoms, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium, carboxyl, -COOM, where M is an ammonium or alkali metal atom or atom alkaline earth metal, or C 3 -C 8 cycloalkyl, C 1 -C 5 alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C 1 -C 6 alkylamino, C 1 -C 5 alkoxycarbonyl, dialkylamino 237, or phenyl, wherein the phenyl ring is unsubstituted or substituted by halogen, cyano, nitro, -0R ^a, -NR ^XX R ^XO, alkyl of 1 to 4 carbon atoms, a formyl group, an alkylcarbonyl group having 1 to 4 carbon atoms , COOR ⁷ with C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or CONR ^S R ⁹ , or R ² and R ³ independently represent C 2 -C 6 alkenyl, alkenyl C 2 -C 6 substituted by halogen, cyano, nitro, C 1 -C 4 alkoxy, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium, C 1 -C 4 trialkylammonium alkyl, carboxyl, -COOM, wherein M is an ammonium group or an alkali k atom or an alkali earth metal atom, or a (C 1 -C 6) alkylamino, (C 2 -C 5) alkoxycarbonyl, (C 2 -C 6) dialkylamino or phenyl group, wherein the phenyl ring may be unsubstituted or substituted by halogen, cyano, nitro, -OR ⁵ , -NR ^XO R ^XX , C 1 -C 4 alkyl, formyl, C 1 -C 4 alkylcarbonyl, COOR ⁷ , C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl alkoxy or CONR ^e R ^9, or the radicals R ² and R ³ independently of one another are an alkynyl radical of 3-6 carbon atoms, alkynyl having 3 to 6 carbon atoms which is substituted by halogen, cyano, nitro, C C 1 -C 8, C 3 -C 6 trialkylsilyl, hydroxy, amino, ammonium a trialkylammonium group having from 1 to 4 238 carbon atoms in each alkyl moiety, carboxyl group, -COOM group, wherein M is an ammonium or alkali metal or alkaline earth metal atom, or a C 1 -C 6 alkylamino group, a C 2 -C 5 alkoxycarbonyl group, a C 2 dialkylamino group up to 6 carbon atoms or a phenyl group, wherein the phenyl ring may be unsubstituted or substituted by halogen, cyano, nitro, -OR ^S , -NR ^XO R ^XX , C 1 -C 4 alkyl, formyl, C 1 -C 4 alkylcarbonyl C 4 -C ⁷ , C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or CONR ^S R ⁹ , or R ² and R ³ each independently represent a formyl group, an alkylcarbonyl group having 1 to 4 carbon atoms; C 8-C 8 alk alkenylcarbonyl, Clo-C s s cycloalkylcarbonyl (C 4 -C 9) -cycloalkenylcarbonyl or C 3 -C 8 -cycloalkylalkylcarbonyl group having from 1 to 6 carbon atoms in the alkyl part, which groups may be unsubstituted or substituted by halogen, cyano, nitro, hydroxy, amino, (C 1 -C 6) alkylamino, (C 2 -C 7) dialkylamino, carboxyl, -COOM, where M is an ammonium or alkali metal or alkaline earth metal atom, or an alkoxycarbonyl group of 2 C 1 -C 8 -cycloalkoxycarbonyl, C 1 -C 8 -alkylaminocarbonyl or C 2 -C 8 -alkylaminocarbonyl, or R ² and R ^{3 are} each independently heterocyclyl, heterocyclylcarbonyl, hete239 a rocyclyl group substituted with halogen, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylcarbonyl, C 1 -C 5 alkylcarbonyloxy, C 1 alkoxycarbonyl C 1 -C 6 aminocarbonyl, C 1 -C 6 alkylaminocarbonyl or C 2 -C 8 dialkylaminocarbonyl, or a heterocyclylcarbonyl substituted with halogen, cyano, nitro, C 1 -C 4 alkyl, alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, aminocarbonyl, C 1 -C 6 alkylamino or C 1 -C 5 alkylcarbonyloxy, or R ² and R ³ independently of each other are represented by the following: a phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenylalkylcarbonyl group having 1 to 6 carbon atoms in the alkyl moiety, a biphenylcarbonyl group having 1 to 6 carbon atoms in the alkyl moiety, a naphthylalkylcarbonyl group having 1 to 6 carbon atoms in the C 2 -C 6 alkyl moiety, up to 6 carbon atoms in the alkenyl moiety, biphenylalkenylcarbonyl having 2 to 6 carbon atoms in the alkenyl moiety or naphthylalkenylcarbonyl having 2 to 6 carbon atoms in the alkenyl moiety, which groups may be unsubstituted or substituted by an alkyl group having 1 to 4 carbon atoms, alkoxy (C 1 -C 4) alkyl, (C 1 -C 4) alkylthio, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkylcarbonyl, halogen, cyano, amino, nitro, -COOR ⁷ , 1-alkoxycarbonyl and 5 carbon atoms, hydroxy, alkylsulfonyl of 1 to 4 carbon 240 atoms, alkylaninokarbonylovou having 1 to 5 carbon atoms or a dialkylaminocarbonyl group having 2 to 6 carbon atoms, or the radicals R ² and R ³ independently of one another are phenyl, naphthyl or heterocyclyl, wherein these groups to be unsubstituted or substituted halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio 4 alkoxy, carboxyl, -CONH _of, alkylaminocarbonyl having 1 to 5 carbon atoms, dialkylaminocarbonyl group having 2 to 7 carbon atoms, alkylcarbonyl having 1 to 4 carbon atoms or alkoxycarbonyl of 1 to C 5 or R ² and R ³ together with the nitrogen to which they are attached form a heterocyclic ring which may be substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, cyano or C 1 -C 4 alkoxy; nitro or R @ ² and R @ ^{3 are} each independently amino, C1 -C4 alkylamino, C2 -C6 dialkylamino, phenylamino, C1 -C5 alkylcarbonylamino, C1 -C5 alkoxycarbonylamino, hydroxy, (C 1 -C 4) alkoxy, (C 1 -C 5) alkylcarbonyloxy or phenoxy, R ⁵ is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 1 -C 6 cyanoalkyl, phenyl, halophenyl, alkoxyphenyl (1-4C) alkoxy, (1-4C) alkyl (1-4C) alkyl, (1-4C) alkylcarbonyl, benzoyl, halobenzoyl, (1-4C) alkylamino, (2-6C) alkylamino C 3 -C 6 trialkylsilyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl, R ⁷ represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl, phenyl, halophenyl, C 2 -C 4 alkoxyalkyl, heterocyclyl or halo-heterocyclyl, R ^s and R® are each independently hydrogen, phenyl, halophenyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 cyanoalkyl; , (C 3 -C 4) alkenyl, (C 4 -C 4) alkynyl or (C 2 -C 4) alkoxyalkyl, or R ® and R ® together with the nitrogen atom to which they are attached form a heterocycle which may: halogen, R ^x0 and R ^xx are each independently hydrogen, phenyl, halophenyl C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 cyanoalkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, alkoxyalkyl C 2 -C 4 -alkyl, formyl, C 1 -C 4 -alkylcarbonyl or phenylcarbonyl, the phenyl The 242 radical in these groups may be substituted by a C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, hydroxy, cyano, nitro or C 1 -C 4 alkoxycarbonyl group, or R ¹⁰ and R ^xx together with the nitrogen atom to which they are attached form a heterocycle which may be halogenated. 6. The compound according to claim 1 5, wherein R ² and R ^{3 are} each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with halogen, hydroxy, amino, ammonium, trialkylammonium having 1 to 4 carbon atoms in each alkyl moiety, a carboxyl group, -COOM, wherein M is an ammonium or alkali metal or alkaline earth metal atom, or a C1 -C5 alkylcarbonyloxy, phenylcarbonyloxy, C1 -C6 alkylamino group , C1 -C5 alkoxycarbonyl or C2 -C6 dialkylamino, or R @ ² and R @ ³ each independently represent a formyl group, an alkylcarbonyl group having 1 to 8 carbon atoms, an alkenylcarbonyl group having 2 to 8 carbon atoms. C 4 -C 9 cycloalkylcarbonyl, cycloalkenylcarbon (C 6 -C 9) -alkyl or C 3 -C 8 cycloalkylalkylcarbonyl-C 1 -C 6 -alkyl, which may be unsubstituted or substituted by halogen, cyano, hydroxy, amino, carboxyl, -COOM where M is 243 ammonium or an alkali metal or an alkaline earth metal, or the radicals R ² and R ³ independently of one another are heterocyclyl, heterocyclylcarbonyl, heterocyclyl which is substituted by halogen, cyano, nitro, alkyl having 1 to 5 carbon C 1 -C 5 alkoxy or C 1 -C 6 alkoxycarbonyl, or a heterocyclylcarbonyl substituted with halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or alkylcarbonyl C 1 -C 4, or R ² and R ³ independently represent phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenylalkylcarbonyl of 1 to 6 carbon atoms in the alkyl moiety, biphenylcarbonyl of 1 to 6 carbon atoms in alkyl C 1 -C 6 naphthylalkylcarbonyl, C 2 -C 6 phenylalkenylcarbonyl, C 2 -C 6 biphenylalkenylcarbonyl or C 2 -C 6 naphthyl alkenylcarbonyl; wherein the groups may be unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 alkylcarbonyl carbon, halogen, cyano, amino, nitro, carboxyl, C 1 -C 5 alkoxycarbonyl, hydroxy or C 1 -C 4 alkylsulfonyl, or R ² and R ^{3 are} each independently phenyl 244, naphthyl or heterocyclyl, which groups may be unsubstituted or substituted by halogen, cyano, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylthio, carboxyl or alkoxycarbonyl C 1 -C 5, or R ² and R ³ together with the nitrogen atom to which they are attached, form a heterocyclic ring which may be substituted with C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or cyano. A compound according to claim 1 6, in which the symbols R ² and R ³ are each a hydrogen atom, or the symbols R ² and R ³ independently of one another are formyl, alkylcarbonyl having 1 to 8 carbon atoms, an alkenylcarbonyl group having 2 to 8 carbon atoms, cycloalkylcarbonyl (C 4 -C 9) cycloalkenylcarbonyl (C 6 -C 9) or C 3 -C 8 cycloalkylalkylcarbonyl (C 1 -C 6) alkyl group, which groups may be unsubstituted or substituted by halogen, cyano, hydroxy or amino group, or the radicals R ² and R ³ independently of one another are phenylcarbonyl, where the phenyl ring is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, alkylthio having 1 to 4 carbon atoms is C1-C4haloalkyl C 1 -C 5 -alkyl, halogen, cyano, nitro, carboxyl, C 1 -C 5 alkoxycarbonyl, hydroxy or C 1 -C 4 alkylsulfonyl. 8. The compound according to claim 1 1, in which X is O or S (O) -, wherein x is 0, 1 or 2, and R ⁴ represents a methyl group which is substituted by halogen, cyano, nitro or OR 4 ^s , or R ⁴ is C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, cycloalkylalkyl (C 3 -C 8) cycloalkyl and (C 1 -C 4) alkyl or (C 1 -C 4) alkyl (C 3 -C 8) cycloalkyl group, which groups may be unsubstituted or substituted by halogen, cyano, nitro, oxo or -OR ^S , or R ⁴ represents a phenyl group which is substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 haloalkyl (C 4 -C 4), (C 1 -C 4) haloalkoxy, (C 1 -C 4) haloalkylthio, (C 2 -C 6) alkoxycarbonylalkoxy, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 6 alkyloxycarbonyl, C 1 -C 6 alkylcarbonyl, -CONH ₂ , formyl, C 1 -C 4 alkylaminocarbonyl C 5 -C 6 dialkylaminocarbonyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, C 3 -C 6 trialkylsilyl, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyloxy 6 carbon atoms, phenoxy, halophenoxy or pyridyloxy, or R ⁴ is biphenyl, naphthyl, heterocyclyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylnaphthyl, C 1 -C 4 phenylalkyl or naphthylalkyl C 1 -C 4 alkyl, which groups may be unsubstituted or substituted by halogen, cyano, nitro, amino, carboxyl, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio (C 1 -C 4), (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 1 -C 4) haloalkylthio, (C 2 -C 6) alkoxycarbonylalkoxy (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfinyl; having 1 to 4 carbon atoms, al (C 1 -C 6) alkyloxycarbonyl, (C 1 -C 6) alkylcarbonyl, -CONH ₂ , formyl, C 1 -C 5 alkylaminocarbonyl, C 2 -C 7 dialkylaminocarbonyl, C 3 -C 6 trialkylsilyl alkylcarbonylamino 247 having 1 to 6 carbon atoms, alkylcarbonyloxy of 1 to 6 carbon atoms, phenoxy, halophenoxy or pyridyloxy, and R ^p is H, alkyl having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, cyanoalkyl having 1 to 6 carbon atoms, phenyl, halophenyl, alkoxyphenyl C 1 -C 4 alkoxy, C 1 -C 4 phenylalkyl, C 1 -C 4 alkylcarbonyl, benzoyl, halobenzoyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino C 3 -C 6 trialkylsilyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl. 9. The compound according to claim 1 8, in which X represents an oxygen atom or a sulfur atom, and R ⁴ represents a methyl group which is substituted by a halogen or a cyano group, or R ⁴ is C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, cycloalkylalkyl (C 3 -C 8) cycloalkyl and (C 1 -C 4) alkyl or (C 1 -C 4) alkyl (C 3 -C 8) cycloalkyl group; The 248 groups may be unsubstituted or substituted by halogen or cyano, or R ⁴ is phenyl which is substituted by halogen, cyano, nitro, amino, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl , (C 1 -C 4) haloalkoxy, (C 2 -C 6) alkoxycarbonylalkoxy, (C 1 -C 4) alkylsulfonyl, (C 1 -C 6) alkyloxycarbonyl, (C 1 -C 6) alkylcarbonyl, formyl, (C 1 -C 6) alkyl group (C 4 -C 6), (C 2 -C 6) dialkylamino, (C 3 -C 6) trialkylsilyl or (C 2 -C 6) alkylcarbonyloxy, or R ⁴ is biphenyl, naphthyl, heterocyclyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkylnaphthyl, C 1 -C 4 phenylalkyl or naphthylalkyl C 1 -C 4 alkyl which may be unsubstituted or substituted by halogen, cyano, nitro, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio , (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 2 -C 6) alkoxycarbonylalkoxy (C 1 -C 4) alkylsulfonyl, (C 1 -C 6) alkyloxycarbonyl (C 1 -C 6) alkylcarbonyl C 6 -C 3 trialkylsilyl or C1 -C6 alkylcarbonyloxy. 249 The 1,2,4,6-thiatriazines of formula I according to claim 9, wherein: X represents an oxygen atom, and R ⁴ is phenyl which is substituted by halogen, cyano, nitro, amino, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl , halomethoxy, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino. A process for the preparation of 1,2,4,6-thiatriazines of the general formula I according to claim 1, characterized in that (1) the compound of the general formula II in which the substituents Hal independently represent a fluorine, chlorine or bromine atom are each by reaction with an organometallic compound of formula III R ^x -M (III) wherein R ^x is as defined in claim 1 and M represents a monovalent or polyvalent metal atom, and 250 (IV) (2a) the resulting compound of formula IV wherein R ¹ is as defined in claim 1 and the substituents Hal independently of each other are fluorine, chlorine or bromine, are reacted with a compound of formula V H-XR ⁴ (V) wherein X and R ⁴ are as defined above to give a compound of formula VI (VI) and (3a) this compound is then transformed by reaction with a compound of formula VII M ^X -NR ² R ³ (VII) wherein R ² R ³ are as defined above and M ^x represents a hydrogen or metal atom to give the final 1,2,4,6-thiatriazine of formula I, or (2b) the compound of formula (IV) with a compound of formula (VII) and (VIII) is reacted to form a compound 251 (VIII) Wherein R ¹ , R ² and R ^{3 have the} meanings defined in claim 1 and Hal represents a fluorine, chlorine or bromine atom, and (3b) this compound is then transformed by reaction with a compound of formula V to give a final 1,2,4 6-thiatriazine of formula I. A herbicidal and plant growth inhibiting composition comprising one or more 1,2,4,6-thiatriazines of the formula I according to claim 1. Composition according to claim 12, characterized in that it contains between 0.1% and 95% of the active compound of the formula I. A method for controlling the growth of unwanted plants, characterized in that an effective amount of an active compound of the formula I according to claim 1, or of a composition comprising the active compound, is applied to the plants or their environment. Method according to claim 14, characterized in that the active substance is applied in an amount of between 0.001 and 5 kg, in particular between 0.005 and 2 kg per hectare. 16. A method for inhibiting the growth of plants, which comprises applying to plants or their environment 252 an effective amount of an active ingredient of the formula I as claimed in claim 1, or a composition comprising the active ingredient. The method of claim 14 for selectively pre- and post-emergence weed control in crops of useful plants. Use of a composition according to claim 12 for selectively pre- and post-emergence weed control in crops of useful plants. 19. A seed which has been treated with the composition of claim 12. 20. The 1,2,4,6-thiatriazines of formula IV Hai N 1 ' R-S N (IV) Hai in which R ¹ is as defined in claim 1, and H 1a, independently of each other, is a fluorine, chlorine or bromine atom. 21. The 1,2,4,6-thiatriazines of formula VI 253 (VI) N-H 1 ' R-S N * // * in N- \ Hal wherein R ¹ , X and R ⁴ have the meanings defined in claim 1, and Hal represents a fluorine, chlorine or bromine atom. 22. The 1,2,4,6-thiatriazines of formula VIII NFvR ³ / R p ' N // (VIII) Hal wherein R ¹ , R ² and R ³ have the meanings defined in claim 1, and Hal represents a fluorine, chlorine or bromine atom.