Herbicidal 1,2,4,6-thiatriazines

Description

The present invention relates to novel, herbicidally active thiatriazine derivatives, processes for their preparation, compositions comprising these compounds, and their use for controlling weeds, in particular in crops of useful plants, for example cereals, maize, rice, cotton, soya, oilseed rape, sorghum, sugar cane, sugar beet, sunflower, vegetables and fodder plants, or for inhibiting plant growth.

Thiatriazine compounds are described, for example, in Z. Chem. 15(5), 193-194 (1975), ibid. 15(2), 57-58 (1975), Chem. Ber. 121, 383-386 (1988), Z. Naturforsch. 43, 763-768 (1988), Chem. Ber. 126, 2601-2607 (1993), J. Am. Chem. Soc. 111, 1180-1185 (1989), DD-A-113 006 and in the inaugural dissertation by W. Jürgler, Philipps-University Marburg/Lahn, 1988 (“1λ

4

- and 1λ

6

-2,4,6-thiatriazines from sulfodiimides”).

Novel and simple synthesis methods for preparing novel diversely substituted thiatriazine derivatives have now been found. In addition to the easy accessibility of diversely substituted thiatriazine derivatives, the low number of synthesis stages is another advantage of the synthesis methods. Herbicidal and growth-inhibiting properties have been found for these thiatriazine derivatives.

The present invention thus relates to compounds of the formula I

in which

R

1

is a group —OR

7

, —NR

90

R

91

or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms;

R

7

is C

1

-C

16

alkyl, C

1

-C

16

alkyl substituted by halogen, NO

2

, CN, C

1

-C

5

alkoxy, C

1

-C

5

alkylthio, C

3

-C

8

cycloalkoxy, C

3

-C

8

cycloalkylthio, C

1

-C

3

trialkylsilyl, C

3

-C

10

alkenyloxy, C

3

-C

5

alkynyloxy, C

1

-C

5

alkylcarbonyloxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkylcarbonyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

4

alkyl, or

R

7

is C

1

-C

16

alkyl substituted by C

3

-C

8

cycloalkyl, C

6

-C

12

bicycloalkyl, C

6

-C

12

chlorobicycloalkyl, C

6

-C

12

bicycloalkenyl or adamantyl, or

R

7

C

1

-C

16

alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring, or

R

7

is C

3

-C

15

alkenyl, C

3

-C

15

alkenyl substituted by halogen, C

1

-C

3

alkoxy, C

3

-C

8

cycloalkyl, C

1

-C

3

trialkylsilyl or substituted or unsubstituted aryl or aryloxy, or

R

7

is C

3

-C

5

alkynyl, C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by halogen, CN, C

1

-C

3

trialkylsilyl, ═O, C

1

-C

6

alkyl, cyano-C

1

-C

5

alkyl, C

1

-C

5

alkyl-CONH—C

1

-C

5

alkyl, phenyl-CONH—C

1

-C

5

alkyl, C

1

-C

5

chloroalkyl, C

1

-C

3

alkoxy, C

1

-C

3

alkylthio, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkoxycarbonyl-C

1

-C

5

alkyl, C

5

-C

7

cycloalkyl, C

2

-C

4

alkenyl, C

2

-C

4

alkynyl, benzyl or C

1

-C

3

halogenoalkyl, or

R

7

is C

5

-C

7

cycloalkenyl, C

5

-C

7

cycloalkenyl substituted by C

1

-C

3

alkyl, or

R

7

is C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkyl substituted by C

1

-C

3

alkyl, cyano or halogen, C

6

-C

12

bicycloalkenyl, C

6

-C

12

bicycloalkenyl substituted by C

1

-C

3

alkyl, or

R

7

is a substituted or unsubstituted non-aromatic heterocyclic ring or an alicyclic ring system;

R

90

and R

91

independently of one another are hydrogen, C

1

-C

12

alkyl, C

1

-C

12

alkyl substituted by halogen, NO

2

, CN, hydroxyl, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

trialkylsilyl, C

1

-C

6

alkylamino, di(C

1

-C

6

alkyl)amino, C

3

-C

7

cycloalkyl,

or a heterocyclic ring, or C

3

-C

10

alkenyl, C

3

-C

10

alkynyl, C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkenyl, C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by C

1

-C

4

alkyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

4

alkyl, with the proviso that R

90

and R

91

are not simultaneously hydrogen; or

R

90

and R

91

, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C

1

-C

4

alkyl, C

1

- or C

2

halogenoalkyl, C

1

- or C

2

hydroxyalkyl, methoxy-C

1

-C

4

alkyl, halogen, hydroxyl, CN, C

1

-C

4

alkoxy, C

1

-C

4

alkylcarbonyl, C

1

- or C

2

halogenoalkyl

C

1

-C

3

alkoxycarbonyl, (C

1

-C

3

alkyl)

2

NCO, di(C

1

-C

4

alkyl)amino or ═O and can additionally be bridged by 1 or 2

groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or

R

90

and R

91

, together with the nitrogen atom to which they are bonded, form a mono- or diunsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C

1

-C

4

alkyl, C

1

- or C

2

halogenoalkyl, halogen, hydroxyl, CN, amino, C

1

-C

4

alkylamino, di(C

1

-C

4

alkyl)amino, phenyl, C

1

-C

4

alkoxy or C

1

-C

3

alkoxycarbonyl and additionally bridged by 1 or 2

groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused;

the radicals R

24

independently of one another are hydrogen or methyl;

R

98

is hydrogen, fluorine, chlorine, bromine, CN, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkoxy-C

1

-C

3

alkyl, C

1

- or C

2

halogenoalkyl, C

1

-C

5

alkyl, NO

2

, C

3

-C

5

alkenyl, cyclopropyl or C

1

- or C

2

halogenoalkoxy;

R

2

is halogen, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylthio, C

1

-C

10

alkylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenylthio or C

3

-C

10

alkenylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R

2

is C

3

-C

5

alkynyloxy, C

3

-C

5

-alkynylthio, C

3

-C

8

cycloalkyl-X—, C

6

-C

12

bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—;

X is —O—, —S—, —SO— or —SO

2

—, or

R

2

is a group R

88

R

89

N—,

R

88

and R

89

independently of one another are hydrogen, C

1

-C

6

alkyl, C

1

-C

6

alkyl substituted by halogen, CN, C

1

-C

3

alkoxy or

C

3

-C

12

cycloalkyl, C

3

-C

10

alkenyl, C

3

-C

10

alkynyl, C

6

-C

12

bicycloalkyl or C

6

-C

12

bicycloalkyl substituted by C

1

-C

3

alkyl;

the radicals R

20

independently of one another are hydrogen or C

1

-C

4

alkyl;

n

7

is 4 or 5;

Y is —O—, —S—, —NH— or —NR

101

—;

R

101

is C

1

-C

4

alkyl, C

1

-C

4

alkylcarbonyl or C

1

-C

3

alkoxycarbonyl; and

R

98

is as defined above;

R

3

is halogen, hydroxyl, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylthio, C

1

-C

10

alkylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenylthio or C

3

-C

10

alkenylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R

3

is C

3

-C

5

alkynyloxy, C

3

-C

5

alkynylthio, C

3

-C

8

cycloalkyl-X—, C

6

-C

12

bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and

X is as defined above,

and stereoisomers of the compounds of the formula I,

excluding the compounds of formulae I

1

to I

7

wherein

R

01

is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl;

R

02

is ethyl or benzyl and

R

03

is ethyl, cyclohexyl or benzyl, or

R

02

and R

03

, together with the nitrogen atom to which they are bonded, form a piperidine ring;

R

04

is chlorine, methylthio, ethylthio, i-propylthio, n-butylthio, i-butylthio, phenylthio or benzylthio;

R

05

is ethoxy, methylthio, ethylthio or phenylthio; and

R

06

is chlorine or cyclohexylamino.

The alkyl groups occurring in the substituent definitions can be straight-chain or branched, which also applies to the alkyl, alkenyl and alkynyl moiety of the halogenoalkyl, halogenoalkenyl, alkenyloxy, alkylcarbonyloxy, alkoxyalkyl-, alkoxyalkenyl-, alkoxycarbonyl-, alkoxycarbonylalkyl-, alkylamino-, dialkylamino-, alkoxyalkoxy-, nitroalkyl-, cyanoalkyl-, hydroxyalkyl-, alkylaminoalkyl-, dialkylaminoalkyl-, cycloalkylalkyl-, heterocyclylalkyl-, alkoxyalkenyloxy-, alkoxycarbonylalkenyloxy-, halogenoalkylthio-, alkoxyalkylthio-, alkenylthio, halogenoalkenylthio-, alkoxyalkenylthio-, halogenoalkylcarbonyl- and halogenoalkoxycarbonyl groups.

Examples of alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl or hexadecyl and branched isomers thereof. These alkyl groups can be substituted by halogen, cyano, nitro, hydroxyl, C

1

-C

3

alkoxy, C

1

-C

6

alkylamino, di(C

1

-C

6

-alkyl)amino, C

3

-C

10

alkenyl, C

3

-C

10

alkynyl, C

3

-C

10

alkenyloxy, C

3

-C

5

alkynyloxy, C

1

-C

3

trialkylsilyl, C

1

-C

6

alkoxycarbonyl, heterocyclyl, C

3

-C

12

cycloalkyl, C

3

-C

8

cycloalkoxy or C

6

-C

10

bicycloalkyl. The alkenyl and alkynyl radicals can be mono- or polyunsaturated.

Examples of alkenyls are allyl, methallyl, 1-methylallyl, but-2-en-1-yl, pent-4-en-1-yl, hex-4-en-1-yl and hept-4-en-1-yl, preferably alkenyl radicals having a chain length of 3 to 6 carbon atoms. The alkenyl groups can be substituted on the saturated carbon atoms, for example by C

1

-C

6

alkoxy or C

3

-C

8

cycloalkyl, and on the saturated or unsaturated carbon atoms by halogen. The alkenyl radicals are preferably bonded to a heteroatom by a saturated carbon atom.

Examples of alkynyls are propargyl, but-3-yn-1-yl, but-2-yn-1-yl, 1-methylpropargyl, 2-methylbutyn-2-yl, pent-4-yn-1-yl or 2-hexynyl, preferably alkynyl radicals having a chain length of 3 to 6 carbon atoms. The alkynyl radicals are preferably bonded to a heteroatom via a saturated carbon atom.

Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. A corresponding statement also applies to halogen in combination with other definitions, such as halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkylcarbonyl, halogenoalkoxycarbonyl, halogenoalkylcarbonyloxy, halogenocycloalkyl or halogenobicycloalkyl.

Halogenoalkyl is alkyl groups which are mono- or polysubstituted, in particular mono- to trisubstituted, by halogen, halogen specifically being iodine and, in particular, fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, pentafluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl.

Alkoxy is, for example, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, and one of the isomeric pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy and decyloxy radicals.

Halogenoalkenyl is alkenyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and, in particular, fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl and 4,4,4-trifluoro-but-2-en-1-yl. Preferred C

3

-C

15

alkenyl radicals which are mono- di- or trisubstituted by halogen are those which have a chain length of 3 to 6 carbon atoms.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl and hexyloxycarbonyl and branched isomers thereof, preferably methoxycarbonyl, ethoxycarbonyl and propoxycarbonyl.

Alkylamino is, for example, methylamino, ethylamino, propyl-, butyl-, pentyl- and hexylamino and their branched isomers.

Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dipropyl-, dibutyl-, dipentyl- and dihexylamino and their branched isomers.

In substituents such as dialkylamino or dialkylaminoalkyl, the alkyl radicals can be identical or different. They preferably have the same meaning. Corresponding statements also apply to the alkyl radicals in dialkylaminocarbonyl and trialkylsilyl substituents.

Alkoxyalkoxy is, for example, methoxymethoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy, propoxyethoxy, butoxyethoxy and butoxybutoxy.

Halogenoalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluorethoxy, 1,1,2,2-tetrafluorethoxy, 2fluorethoxy, 2-chloroethoxy and 2,2,2-trichloroethoxy.

Alkylthio is, for example, methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, nonylthio or decylthio and branched isomers thereof.

Alkenyloxy is, for example, allyloxy, 1-methylallyloxy, methallyloxy, but-2-en-1-yloxy or hex-2-en-1-yloxy. Alkenyl radicals having a chain length of 3 to 6 carbon atoms are preferred.

Alkynyloxy is, for example, propargyloxy, 1-methylpropargyloxy, but-3-yn-1-yloxy or pent-4-yn-1-yloxy.

Alkenylthio is, for example, allylthio, methallylthio, but-3-en-1-ylthio, pent-4-en-1-ylthio or hex-2-en-1-ylthio.

Alkynylthio is, for example, propargylthio, 1-methylpropargylthio, but-3-yn-1-ylthio, pent-4-yn-1-ylthio or hex-2-yn-1-ylthio.

Suitable cycloalkyl substituents contain 3 to 12 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl or cyclododecyl. Corresponding cycloalkenyl substituents can be mono- or else polyunsaturated, for example cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl or cyclooctatetraenyl.

Cycloalkyl and also cycloalkenyl substituents can, unless stated otherwise, be substituted by C

1

-C

4

alkyl and contain fused-on aryl rings.

If alkyl, alkenyl or alkynyl occur as substituents on a cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, phenyl, biphenyl, naphthyl or heterocyclyl, these ring systems can also be polysubstituted by alkyl, alkenyl or alkynyl.

If R

20

, R

24

, R

25

, R

97

, R

98

or R

99

occur on phenyl, naphthyl or heteroaryl, these ring systems can also be polysubstituted by R

20

, R

24

, R

25

, R

97

, R

98

or R

99

.

If R

20

, R

24

, R

25

, R

98

or R

100

occur on alicyclic or carbocyclic rings, these ring systems can also be polysubstituted by R

20

, R

24

, R

25

, R

98

or R

100

.

Carbocyclic radicals are to be understood as meaning saturated and unsaturated, mono- and polycyclic ring systems which consist of cycloalkanes, cycloalkenes, polycycloalkanes and polycycloalkenes. Carbocyclic radicals preferably contain 3 to 12 carbon atoms, for example cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclohexene, cycloheptane, cyclooctane, cyclononane, cyclodecane, cyclododecane and cis- and trans-decalin, it being possible for these carbocyclic radicals, unless stated otherwise, to be substituted by C

1

-C

4

alkyl.

Heterocyclyl is to be understood as meaning mono- and polycyclic ring systems which, in addition to carbon atoms, contain at least one heteroatom, such as nitrogen, oxygen or sulfur. They can be saturated or unsaturated and substituted by C

1

-C

3

alkyl, halogen or ═O. Such ring systems preferably contain 3 to 12 ring atoms. This also applies to those heterocyclic radicals which, as in the case of groups such as —NR

90

R

91

, are formed by 2 substituents bonded to a nitrogen atom.

Examples of N-heterocyclic radicals onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused or spiro-bonded and which contain or do not contain further heteroatoms, in the definition of R

1

, are:

in which the radicals R

20

independently of one another are hydrogen, C

1

-C

4

alkyl or C

1

-C

3

alkoxy;

R

25

is hydrogen, chlorine, methyl or methoxy;

R

100

is hydrogen or C

1

-C

3

alkyl;

Y, is —O—, —S— or —NR

30

;

R

30

is hydrogen, methyl, C

1

-C

3

alkylcarbonyl or (C

1

-C

3

alkyl)

2

NCO—;

n

1

is 1, 2, 3, 4 or 5;

n

2

is 0, 1 or 2; and

n

3

is a number from 3 to 10. The hetererocyclic radical is bonded to the thiatriazine ring via its nitrogen atom.

Examples of aryl, aryloxy, arylmethyleneoxy, arylcarbonyl-, arylcarbonyloxy or aryloxycarbonyl ring systems in the definition of R

2

, R

3

, R

7

, R

13

, R

94

and R

97

are:

in which R

25

is as defined above;

R

99

is hydrogen, halogen, NO

2

, CN, C

1

-C

5

alkyl, C

1

-C

6

alkoxy, C

1

- or C

2

halogenoalkoxy, C

1

-C

6

-alkenyloxycarbonyl, C

1

-C

3

alkylthio,

C

1

-C

6

alkoxycarbonyl, NH

2

, C

1

-C

3

alkyl-CONH, di(C

1

-C

6

alkyl)amino or C

1

-C

6

alkylamino;

R

98

is hydrogen, fluorine, chlorine, bromine, CN, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

-alkoxy-C

1

-C

3

-alkyl, C

1

- or C

2

-halogenoalkyl, C

1

-C

5

-alkyl, NO

2

, C

3

-C

5

alkenyl, cyclopropyl or C

1

- or C

2

halogenoalkoxy; and

n

6

is 3, 4, 5 or 6.

Examples of heterocyclic rings R

7

and R

2

or R

3

bonded to alkyl or alkoxy are:

in which R

98

and R

100

are as defined above;

R

24

is hydrogen or methyl; and

R

101

is C

1

-C

4

alkyl, C

1

-C

4

alkylcarbonyl or C

1

-C

3

-alkoxycarbonyl.

Examples of non-aromatic heterocyclic rings in the definition of R

7

are:

in which R

100

and R

101

are as defined above.

Alicyclic ring systems in the definition of P

7

are saturated and unsaturated, mono- and polycyclic ring systems containing bridge bonds and heteroatoms, such as nitrogen, oxygen or sulfur. Examples of such alicyclic ring systems are:

in which R

21

and R

22

independently of one another are hydrogen or C

1

-C

4

alkyl;

n

9

is 3 or 4; and

R

20

, R

24

, R

25

, R

98

, R

100

, R

101

and n

6

are as defined above.

Examples of heterocyclic rings R

90

and R

91

, which are independent of one another, bonded to alkyl are:

in which R

25

and R

100

are as defined above.

Saturated and unsaturated and substituted or unsubstituted mono- or bicyclic heterocyclic radicals formed from —NR

90

R

91

include, for example, pyrrolidyl, dimethylpyrrolidyl, piperidyl, morpholinyl, dimethylmorpholinyl, thiomorpholinyl, cis- and trans-decahydro(iso)quinolyl, tetrahydropyridyl, 1,2,3,4-tetrahydro(iso)quinolyl, 1-methylpiperazinyl, perhydroindolyl, 3-pyrrolinyl, hexahydro-azepinyl, aziridyl, azeudyl, 4-piperidonyl and homopiperazinyl, it being possible for these heterocyclic radicals to have 1 or 2 further carbocyclic, heterocyclic or aromatic rings, for example cyclohexane, (nor-)bornane, cyclopentane, cycloheptane, cyclododecane or phenyl, fused-on or spiro-linked carbocyclic rings, for example cyclohexane or (nor-)bornene.

Further examples of saturated, substituted or unsubstituted heterocyclic rings formed from —NR

90

R

91

which contain or do not contain heteroatoms or which can additionally be bridged with 1 or 2 groups

are:

Preferred examples in which R

90

and R

91

, together with the nitrogen atom, form a ring are pyrrolidyl, piperidyl, dimethylpiperidyl, ethoxycarbonylpiperidyl, morpholinyl, dimethylmorpholinyl, cis- and trans-decahydro(iso)quinolyl and 1,2,3,4-tetrahydro(iso)quinolyl.

Examples of aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X— R

2

and R

3

are:

in which X is —O—, —S—, —SO— or —SO

2

—;

X

2

is —O—, —S— or —NR

100

—;

R

20

, R

24

, R

98

and R

100

are as defined above;

R

92

is hydrogen or C

1

-C

4

alkyl;

R

93

is hydrogen, C

1

-C

4

alkyl, hydroxyl, C

1

-C

4

alkoxy or C

1

-C

4

alkylthio; R

97

is hydrogen, halogen, NO

2

, CN, C

3

-C

6

cycloalkoxy, C

1

-C

10

alkyl, C

1

-C

10

alkyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyl, C

3

-C

10

alkenyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

-alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyl, C

1

-C

10

alkylcarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxycarbonyl, C

1

-C

10

alkoxycarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyloxy or C

1

-C

10

alkylcarbonyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R

97

is CHO, C

3

-C

8

-cycloalkyl, C

1

-C

4

alkylthio, C

3

- or C

4

alkenylthio, (R

94

)

2

N—, (R

95

)

2

N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

in which R

20

, R

24

, R

25

, R

98

, R

100

, R

101

, X, n

6

and n

9

are as defined above.

Examples of nonaromatic heterocyclyl-X— R

2

and R

3

are:

in which R

24

, X, R

100

and R

101

are as defined above.

Examples of cyclic radicals R

11

, in the compounds of the formula XII in the preparation process, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contain or do not contain heteroatoms are:

In the definitions cyanoalkyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl, alkoxycarbonylalkoxy and alkenyloxycarbonyl, the cyano or carbonyl carbon atom is not included in the particular lower and upper limits stated for the number of carbons.

Unless stated specifically,

1

H— and

13

C-NMR spectra (Tables 1-6) were recorded with a 300 MHz spectrometer in CDCl

3

.

The compounds of the formula I in which R

2

and R

3

differ from one another have a centre of asymmetry in the sulfur atom of the thiatriazine ring.

Furthermore, asymmetric centres can be present in the substituents of the thiatriazine ring, for example in the definition of R

1

or R

7

. This means that diastereomers can be formed, which can sometimes be separated by column chromatography, as shown, for example, in the tabular examples Compound Nos. 5.45/5.46, 6.6, 6.10, 6.55/6.56, 6.92/6.93, 6.120/6.121 and 6.153/6.154.

If substituents are bonded via a wavy line to a ring system in the formulae, for example in the definition of R

1

, this means that all conformations or geometric isomerisms (‘up’ and ‘down’, or ‘equatorial’ and ‘axial’) are possible for these substituents.

Unless chiral starting materials are used, the compounds of the formula I are in general obtained as racemates in the process described in this application, and these are separated by customary separation processes, for example chromatographic processes, for example high pressure liquid chromatography (HPLC) over acetylcellulose, on the basis of physico-chemical properties. In the present invention, the active compounds of the formula I are to be understood as meaning both the pure optical antipodes and the racemates. Unless the individual optical antipodes are referred to specifically, those racemic mixtures which are formed in the preparation process described are to be understood under the formula given. If an aliphatic C═C double bond is present or if alicyclic or carbocyclic rings contain substituents, geometric isomerism may also occur.

The formula I is intended to include all these possible isomers, enantiomers and diastereoisomers and mixtures thereof.

Preferred compounds are those of the formula I

in which the radicals R

20

, R

25

, R

100

, Y

1

, n

1

, n

2

and n

3

are as defined above.

Suitable substituted or unsubstituted bicycloalkyl and bicycloalkenyl substituents contain 6 to 12 carbon atoms and are, for example:

in which R

24

is as defined above.

The substituents in composite definitions, for example cycloalkoxy, cycloalkylalkyl, cycloalkyl-X—, bicycloalkylalkyl, bicycloalkyl-X—, alkylcarbonyl, alkylcarbonyloxy, cycloalkylalkenyl, cycloalkenylalkyl, alkoxyalkyl, alkoxyalkenyl, halogenobicycloalkyl, alkenyloxycarbonyl, alkenyloxyalkoxy, alkoxycarbonylalkoxy, alkylaminoalkyl, dialkylaminoalkyl, heterocyclylalkyl, heterocyclyl-X—, halogenoalkenyloxy, alkoxyalkenyloxy, alkenyloxyalkenyloxy, alkoxycarbonylalkenyloxy, halogenoalkylthio, alkenyloxyalkylthio, alkoxycarbonylalkylthio, halogenoalkenylthio, alkoxyalkenylthio, alkenyloxyalkenylthio, alkoxycarbonylalkenylthio, halogenoalkylcarbonyl, alkoxyalkylcarbonyl, alkenyloxyalkylcarbonyl, alkoxycarbonylalkylcarbonyl, halogenoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyloxyalkoxycarbonyl, alkoxycarbonylalkoxycarbonyl, halogenoalkylcarbonyloxy, alkoxyalkylcarbonyloxy, alkenyloxyalkoxycarbonyloxy and alkoxycarbonylalkylcarbonyloxy can also be assigned corresponding definitions.

in which

R

1

is a group —OR

7

, —NR

90

R

91

, or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms;

R

7

is C

1

-C

16

alkyl, C

1

-C

16

alkyl substituted by halogen, NO

2

, CN, C

1

-C

5

alkoxy, C

1

-C

5

alkylthio, C

3

-C

8

cycloalkoxy, C

1

-C

3

trialkylsilyl, C

3

-C

10

alkenyloxy, C

3

-C

5

alkynyloxy, C

1

-C

5

alkyl-carbonyloxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkylcarbonyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

4

alkyl, or

R

7

is C

1

-C

16

alkyl substituted by C

3

-C

8

cycloalkyl, C

6

-C

12

bicycloalkyl, C

6

-C

12

chlorobicycloalkyl, C

6

-C

12

bicycloalkenyl or adamantyl, or

R

7

is C

1

-C

16

alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring, or

R

7

is C

3

-C

15

alkenyl, C

3

-C

15

alkenyl substituted by halogen, C

1

-C

3

alkoxy, C

3

-C

8

cycloalkyl or substituted or unsubstituted aryl or aryloxy, or

R

7

is C

3

-C

5

alkynyl, C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by halogen, CN, C

1

-C

3

-trialkylsilyl, ═O, C

1

-C

6

alkyl, cyano-C

1

-C

5

alkyl, C

1

-C

5

alkyl-CONH—C

1

-C

5

alkyl, phenyl-CONH—C

1

-C

5

alkyl, C

1

-C

5

chloroalkyl, C

1

-C

3

alkoxy, C

1

-C

3

alkylthio, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkoxycarbonyl-C

1

-C

5

alkyl, C

5

-C

7

cycloalkyl, C

2

-C

4

alkenyl, C

2

-C

4

alkynyl, benzyl or C

1

-C

3

halogenoalkyl, or

R

7

is C

5

-C

7

cycloalkenyl, C

5

-C

7

cycloalkenyl substituted by C

1

-C

3

alkyl, or

R

7

is C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkyl substituted by C

1

-C

3

alkyl or halogen, C

6

-C

12

bicycloalkenyl, C

6

-C

12

bicycloalkenyl substituted by C

1

-C

3

alkyl, or

R

7

is a substituted or unsubstituted nonaromatic heterocyclic ring or an alicyclic ring system;

R

90

and R

91

independently of one another are hydrogen, C

1

-C

12

alkyl, C

1

-C

12

alkyl substituted by halogen, NO

2

, CN, hydroxyl, C

1

-C

3

alkoxy, C

1

-C

3

trialkylsilyl, C

1

-C

6

alkylamino, di(C

1

-C

6

-alkyl)amino, C

3

-C

7

cycloalkyl,

or a heterocyclic ring, or C

3

-C

10

alkenyl, C

3

-C

10

alkynyl, C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkenyl, C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by C

1

-C

4

alkyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

4

alkyl, with the proviso that R

90

and R

91

are not simultaneously hydrogen; or

R

90

and R

91

, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C

1

-C

4

alkyl, C

1

- or C

2

-halogenoalkyl, methoxy-C

1

-C

4

alkyl, halogen, hydroxyl, CN, C

1

-C

4

alkoxy, C

1

-C

4

-alkylcarbonyl, C

1

- or C

2

halogenoalkyl,

C

1

-C

3

alkoxycarbonyl, (C

1

-C

3

alkyl)

2

NCO, di(C

1

-C

4

alkyl)amino or ═O and can additionally be bridged by 1 or 2

groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or

R

90

and R

91

, together with the nitrogen atom to which they are bonded, form a monounsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C

1

-C

4

alkyl, C

1

- or C

2

halogenoalkyl, halogen, hydroxyl, CN, amino, C

1

-C

4

alkylamino, di(C

1

-C

4

alkyl)amino, phenyl, C

1

-C

4

alkoxy or C

1

-C

3

alkoxycarbonyl and is additionally bridged by 1 or 2

groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused;

the radicals R

24

independently of one another are hydrogen or methyl;

R

98

is hydrogen, fluorine, chlorine, bromine, CN, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

-alkoxy-C

1

-C

3

alkyl, C

1

- or C

2

halogenoalkyl, C

1

-C

5

alkyl, NO

2

, C

3

-C

5

alkenyl, cyclopropyl or C

1

- or C

2

halogenoalkoxy;

R

2

is halogen, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylthio, C

1

-C

10

alkylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenylthio or C

3

-C

10

alkenylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R

2

is C

3

-C

5

alkynyloxy, C

3

-C

5

alkynylthio, C

3

-C

8

cycloalkyl-X—, C

6

-C

12

bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; X is —O—, —S—, —SO— or —SO

2

—, or

R

2

is a group R

88

R

89

N—,

R

88

and R

89

independently of one another are hydrogen, C

1

-C

6

alkyl, C

1

-C

6

alkyl substituted by halogen, CN, C

1

-C

3

alkoxy or

C

3

-C

12

cycloalkyl, C

3

-C

10

alkenyl, C

3

-C

10

alkynyl, C

6

-C

12

bicycloalkyl or C

6

-C

12

bicycloalkyl substituted by C

1

-C

3

alkyl;

the radicals R

20

independently of one another are hydrogen or C

1

-C

4

alkyl;

n

7

is 4 or 5;

Y is —O—, —S—, —NH— or —NR

101

—;

R

101

is C

1

-C

4

alkyl, C

1

-C

4

alkylcarbonyl or C

1

-C

3

alkoxycarbonyl and

R

98

is as defined above; and

R

3

is halogen, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylthio, C

1

-C

10

alkylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenylthio or C

3

-C

10

alkenylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R

3

is C

3

-C

5

alkynyloxy, C

3

-C

5

alkynylthio, C

3

-C

8

cycloalkyl-X—, C

6

-C

12

bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and X is as defined above.

Preferred compounds of the formula I are also those in which

in which the radicals R

20

independently of one another are hydrogen or C

1

-C

4

alkyl;

R

25

is hydrogen, chlorine, methyl or methoxy;

R

100

is hydrogen or C

1

-C

3

alkyl;

Y

1

is —O—, —S— or —NR

30

;

R

30

is hydrogen, methyl, C

1

-C

3

alkylcarbonyl or (C

1

-C

3

alkyl)

2

NCO;

n

1

is 1, 2, 3, 4 or 5;

n

2

is 0, 1 or 2; and

n

3

is a number from 3 to 10.

Preferred compounds of the formula I are also those in which

R

1

is the group —OR

7

, in which

R

7

is as defined under formula I and

R

2

and R

3

independently of one another are chlorine, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylthio, C

1

-C

10

alkylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenylthio or C

3

-C

10

alkenylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R

2

and R

3

independently of one another are C

3

-C

5

alkynyloxy, C

3

-C

5

alkynylthio, C

3

-C

8

cycloalkyl-X—, C

6

-C

12

bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.

Compounds of the formula I which are likewise preferred are those in which

R

1

is the group —OR

7

;

R

2

is a group R

88

R

89

N—,

and R

3

is aryl-X—,

phthalidyl-X—, biphenyl-X—, or heteroaryl-X—, in which

R

7

, R

20

, R

88

, R

89

, Y, n

7

and X are as defined under formula I.

Thiatriazine derivatives of the formula I which are furthermore preferred are those in which R

1

is a group —NR

90

R

91

or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms.

R

2

is a group R

88

R

89

N—,

and R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, in which R

20

, R

88

, R

89

, Y, n

7

and X are as defined under formula I.

Particularly preferred thiatriazine derivatives of the formula I are those in which

R

1

is a group —OR

7

;

R

7

C

1

-C

16

alkyl, C

1

-C

16

alkyl substituted by halogen, NO

2

, CN, C

1

-C

5

alkoxy, C

1

-C

5

alkylthio, C

3

-C

8

cycloalkoxy, C

1

-C

3

trialkylsilyl, C

3

-C

10

alkenyloxy, C

3

-C

5

alkynyloxy, C

1

-C

5

alkylcarbonyloxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkylcarbonyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

4

alkyl, or

R

7

is C

1

-C

16

alkyl substituted by C

6

-C

12

bicycloalkyl, C

6

-C

12

chlorobicycloalkyl,

C

6

-C

12

bicycloalkenyl or adamantyl, or R

7

is C

1

-C

16

alkyl substituted by

in which R

24

is hydrogen or methyl;

R

98

is hydrogen, fluorine, chlorine, bromine, CN, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkoxy-C

1

-C

3

alkyl, C

1

- or C

2

halogenoalkyl, C

1

-C

5

alkyl, NO

2

, C

3

-C

5

alkenyl, cyclopropyl or C

1

- or C

2

halogenoalkoxy;

R

99

is hydrogen, halogen, NO

2

, CN, C

1

-C

5

alkyl, C

1

-C

6

alkoxy, C

1

-C

6

alkenyloxycarbonyl, C

1

-C

3

alkylthio,

C

1

-C

6

alkoxycarbonyl, NH

2

, C

1

-C

3

alkyl-CONH, di(C

1

-C

6

alkyl)amino or C

1

-C

6

alkylamino;

R

100

is hydrogen or C

1

-C

3

alkyl; and

R

101

is C

1

-C

4

alkyl, C

1

-C

4

alkylcarbonyl or C

1

-C

3

alkoxycarbonyl; or

R

7

is C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by halogen, CN, C

1

-C

3

trialkylsilyl, ═O, C

1

-C

6

alkyl, cyano-C

1

-C

5

alkyl, C

1

-C

5

alkyl-CONH—C

1

-C

5

alkyl, phenyl-CONH—C

1

-C

5

alkyl, C

1

-C

5

chloroalkyl, C

1

-C

3

alkoxy, C

1

-C

3

alkylthio, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkoxycarbonyl-C

1

-C

5

alkyl, C

5

-C

7

cycloalkyl, C

2

-C

4

alkenyl, C

2

-C

4

alkynyl, benzyl or C

1

-C

3

halogenoalkyl, C

5

-C

7

-cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

3

alkyl, or

R

7

is C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkyl substituted by C

1

-C

3

alkyl or halogen,

C

6

-C

12

bicycloalkenyl or C

6

-C

12

bicycloalkenyl substituted by C

1

-C

3

alkyl, or

R

7

is a substituted or unsubstituted nonaromatic heterocyclic ring or an alicyclic ring system;

R

2

is a group R

88

R

89

N—;

R

88

and R

89

independently of one another are hydrogen, C

1

-C

6

alkyl, C

1

-C

6

alkyl substituted by halogen, CN, C

1

-C

3

alkoxy or

C

3

-C

12

cycloalkyl, C

3

-C

10

alkenyl,

C

3

-C

10

alkynyl, C

6

-C

12

bicycloalkyl or C

6

-C

12

bicycloalkyl substituted by C

1

-C

3

alkyl; and

R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.

Of these, especially preferred thiatriazine derivatives of the formula I are those in which

R

7

is C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by halogen, CN, C

1

-C

6

alkyl, cyano-C

1

-C

5

alkyl, C

1

-C

3

alkoxy or C

1

-C

3

halogenoalkyl, or R

7

is C

5

-C

7

cycloalkenyl or C

5

-C

7

cyclo-alkenyl substituted by methyl, or

R

7

is C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkyl substituted by methyl or chlorine,

C

6

-C

12

bicycloalkenyl or C

6

-C

12

bicycloalkenyl substituted by methyl, or

in which

R

100

is hydrogen or C

1

-C

3

alkyl; and

R

101

is C

1

-C

4

alkyl, C

1

-C

4

alkylcarbonyl or C

1

-C

3

alkoxycarbonyl; or

in which R

20

is hydrogen or C

1

-C

4

alkyl;

R

21

and R

22

independently of one another are hydrogen or C

1

-C

4

alkyl;

R

24

is hydrogen or methyl;

R

25

is hydrogen, chlorine, methyl or methoxy;

R

98

is hydrogen, fluorine, chlorine, bromine, CN, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

alkoxy-C

1

-C

3

alkyl, C

1

- or C

2

halogenoalkyl, C

1

-C

5

alkyl, NO

2

, C

3

-C

5

alkenyl, cyclopropyl or C

1

- or C

2

-halogenoalkoxy;

n

6

is 3, 4, 5 or 6;

n

9

is 3 or 4; and

R

100

and R

101

are as defined above;

R

2

is a group R

88

R

89

N—;

R

88

and R

89

independently of one another are hydrogen or C

1

-C

6

alkyl and

in which X is —O— or —S—;

X

2

is —O—, —S— or —NR

100

—;

R

20

, R

24

and R

100

are as defined above;

R

92

is hydrogen or C

1

-C

4

alkyl;

R

93

is hydrogen, C

1

-C

4

alkyl, hydroxyl, C

1

-C

4

alkoxy or C

1

-C

4

alkylthio;

R

97

is hydrogen, halogen, NO

2

, CN, C

3

-C

6

cycloalkoxy, C

1

-C

10

alkyl, C

1

-C

10

calkyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyl, C

3

-C

10

alkenyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyl, C

1

-C

10

alkylcarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxycarbonyl, C

1

-C

10

alkoxycarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyloxy or C

1

-C

10

alkylcarbonyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

-alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R

97

is CHO, C

3

-C

8

cycloalkyl, C

1

-C

4

alkylthio, C

3

- or C

4

alkenylthio, (R

94

)

2

N—, (R

95

)

2

N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

the radicals R

94

independently of one another are hydrogen, C

1

-C

10

alkyl, C

3

-C

8

cycloalkyl, C

1

-C

10

alkylcarbonyl or substituted or unsubstituted arylcarbonyl; the radicals

R

95

independently of one another are hydrogen, C

1

-C

5

alkyl or C

3

-C

8

cycloalkyl;

n

5

is a number from 5 to 12; and

R

98

is as defined above.

Of these, those compounds in which X and X

2

are —O— are especially important.

Particularly preferred compounds of the formula I are also those in which

R

1

is a group —NR

90

R

91

or

R

90

and R

91

independently of one another are C

1

-C

12

alkyl, C

1

-C

12

alkyl substituted by halogen, CN or C

1

-C

3

alkoxy, C

6

-C

12

bicycloalkyl, C

6

-C

12

bicycloalkenyl, C

3

-C

12

cycloalkyl, C

3

-C

12

cycloalkyl substituted by C

1

-C

4

alkyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by C

1

-C

4

alkyl;

the radicals R

20

independently of one another are hydrogen or C

1

-C

4

alkyl;

n

1

is 1, 2, 3, 4 or 5;

n

2

is 0, 1 or 2; and

n

3

is a number from 3 to 10;

R

2

is a group R

88

R

89

N—;

R

88

and R

89

independently of one another are hydrogen or C

1

-C

6

alkyl and

in which X is —O—, —S—, —SO— or —SO

2

—;

X

2

is —O—, —S— or —NR

100

—;

R

100

is hydrogen or C

1

-C

3

alkyl;

R

20

is as defined above;

R

24

is hydrogen or methyl;

R

92

is hydrogen or C

1

-C

4

alkyl;

R

93

is hydrogen, C

1

-C

4

alkyl, C

1

-C

4

alkoxy or C

1

-C

4

alkylthio;

R

97

is hydrogen, halogen, NO

2

, CN, C

3

-C

6

cycloalkoxy, C

1

-C

10

alkyl, C

1

-C

10

alkyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyl, C

3

-C

10

alkenyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

-alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyl, C

1

-C

10

alkylcarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxycarbonyl, C

1

-C

10

alkoxycarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyloxy or C

1

-C

10

alkylcarbonyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

-alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R

97

is CHO, C

3

-C

8

cycloalkyl, C

1

-C

4

alkylthio, C

3

- or C

4

alkenylthio, (R

94

)

2

N—, (R

95

)

2

N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

the radicals R

94

independently of one another are hydrogen, C

1

-C

10

alkyl, C

3

-C

8

cycloalkyl, C

1

-C

10

alkylcarbonyl or substituted or unsubstituted arylcarbonyl;

the radicals R

95

independently of one another are hydrogen, C

1

-C

5

alkyl or C

3

-C

8

cycloalkyl;

n

5

is a number from 5 to 12; and

R

98

is hydrogen, fluorine, chlorine, bromine, CN, C

1

-C

3

alkoxy, C

1

-C

3

alkoxycarbonyl, C

1

-C

3

-alkoxy-C

1

-C

3

alkyl, C

1

- or C

2

halogenoalkyl, C

1

-C

5

alkyl, NO

2

, C

3

-C

5

alkenyl, cyclopropyl or C

1

- or C

2

halogenoalkoxy.

Especially preferred compounds of these are those in which R

1

is a group

—NR

90

R

91

or

R

90

and R

91

independently of one another are C

1

-C

12

alkyl, C

1

-C

12

alkyl substituted by halogen, CN or C

1

-C

3

alkoxy, C

3

-C

8

cycloalkyl, C

3

-C

8

cycloalkyl substituted by methyl, C

5

-C

7

cycloalkenyl or C

5

-C

7

cycloalkenyl substituted by methyl;

the radicals R

20

independently of one another are hydrogen or methyl;

n

1

is 2, 3 or 4;

n

2

0 or 1; and

n

3

is 3, 4 or 5;

R

2

is a group R

88

R

89

N—;

R

88

and R

89

independently of one another are hydrogen or C

1

-C

3

alkyl; and

in which X is —O— or —S—;

R

97

is hydrogen, halogen, NO

2

, CN, C

1

-C

10

alkyl, C

1

-C

10

alkyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyl, C

3

-C

10

alkenyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkoxycarbonyl, C

1

-C

10

alkoxycarbonyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylcarbonyloxy or C

1

-C

10

alkylcarbonyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy or substituted or unsubstituted aryl or aryloxy, or R

97

is (R

94

)

2

N—, (R

95

)

2

N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl;

the radicals R

94

independently of one another are hydrogen, C

1

-C

4

alkyl, C

3

-C

8

cycloalkyl, C

1

-C

5

alkylcarbonyl or substituted or unsubstituted arylcarbonyl; and

the radicals R

95

independently of one another are hydrogen, C

1

-C

3

alkyl or C

3

-C

6

cycloalkyl.

Especially preferred individual compounds from the scope of formula I are:

3-amino-5-pentafluorophenoxy-1-(trans-3,3,5-trimethylcyclohexanolyl)thiatriazine;

3-amino-5-pentafluorophenoxy-1-[(N-cis-3,3,5-trimethylcyclohexyl)methylamino]thiatriazine;

3-amino-5-pentafluorophenoxy-1-octamethyleneimino-thiatriazine;

3-amino-5-pentafluorophenoxy-1-decahydroquinolyl-thiatriazine;

3-amino-5-pentafluorophenoxy-1-tetrahydroisoquinolyl-thiatriazine; and

the compound of the formula

The compounds of the formula I can be prepared on the one hand by process steps known per se using known starting materials, and on the other hand by processes which are not known per se. The latter processes which are not known per se comprise a procedure in which, for preparation of compounds of the formula I in which R

1

is the group R

7

; R

2

and R

3

independently of one another are halogen, C

1

-C

10

alkoxy, C

1

-C

10

alkoxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyloxy, C

3

-C

10

alkenyloxy substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

1

-C

10

alkylthio, C

1

-C

10

alkylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenylthio or C

3

-C

10

alkenylthio substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R

2

and R

3

independently of one another are C

3

-C

5

alkynyloxy, C

3

-C

5

alkynylthio, C

3

-C

8

cycloalkyl-X—, C

8

-C

12

bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined under formula I,

a

1

) 1,3,5-trichlorthiatriazine is used as the starting substance, and this is converted with an alcohol of the formula XVII

R

7

—OH (XVII),

in which R

7

is as defined under formula I,

if appropriate in the presence of an equimolar amount of base and an inert organic solvent, into the compound of the formula VII

in which R

7

is as defined,

and this compound is then either

b

1

) reacted with a compound of the formula XXIII

R

14

—X

1

H (XXIII),

in which R

14

is C

1

-C

10

alkyl, C

1

-C

10

alkyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

1

-C

6

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyl or C

3

-C

10

alkenyl substituted by halogen, CN, NO

2

, C

1

-C

6

alkoxy, C

3

-C

6

alkenyloxy, C

1

-C

6

alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

5

alkynyl, C

3

-C

8

cycloalkyl, C

6

-C

12

bicycloalkyl, heterocyclyl or alicyclyl and X

1

is oxygen or sulfur,

in the presence of an equimolar amount of base and an inert organic solvent, or

b

2

) converted with a compound of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

is an aryl, phthalidyl, biphenyl or heteroaryl radical; and

X

1

is oxygen or sulfur,

in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula VI

in which R

3

is —X

1

—R

12

,

and this compound is either

c

2

) reacted with the compound of the formula XXIII

R

14

—X

1

H (XXIII),

in which R

14

and X

1

are as defined above,

in the presence of an equimolar amount of base and an inert organic solvent, or

c

3

) converted with the compound of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

and X

1

are as defined above,

in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula V

in which R

3

is —X

1

—R

12

and

R

7

, X

1

and R

12

are as defined above,

and this compound is then

d

3

) reacted with the compound of the formula XXIII

R

14

—X

1

H (XXIII),

in which R

14

and X

1

are as defined,

in the presence of an equimolar amount of base and in an inert organic solvent, or the compound of the formula VII

b

3

) converted with 2 mol of compound of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

and X

1

are as defined,

in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V, and this compound is then reacted in a manner analogous to that described under d

3

), or

a

2

) 1,3,5-trichlorothiatriazine is converted with a C

6

-C

12

bicycloalkyl epoxide, a C

6

-C

12

bicycloalkyl epoxide substituted by C

1

-C

3

alkyl or an epoxide of the formula XVIII or XIX

in which the radicals R

13

independently of one another are hydrogen, C

3

-C

8

alkenyl, C

1

-C

14

alkyl, C

1

-C

14

alkyl substituted by halogen, NO

2

, CN, C

1

-C

5

alkoxy, aryloxy or C

1

-C

3

alkoxycarbonyl;

the radicals R

23

independently of one another are hydrogen or C

1

-C

6

alkyl;

n

8

is a number from 3-10; and

n

11

is 1 or 2,

in an inert organic solvent, into the compound of the formula VII in which R

7

is C

2

-C

16

-b-chloroalkyl, C

2

-C

16

-b-chloroalkyl substituted by halogen, NO

2

, CN, C

1

-C

5

alkoxy, aryloxy or C

1

-C

3

alkoxycarbonyl, C

5

-C

12

-b-chlorocycloalkyl or C

5

-C

12

-b-chlorocycloalkyl substituted by C

1

-C

6

alkyl,

and this compound reacted further in a manner analogous to that described under b

1

); b

2

) and c

2

); b

2

), c

3

) and d

3

); or b

3

) and d

3

), or

a

3

) 1,3,5-trichlorothiatriazine is reacted with an alcohol of the formula XVII

R

7

—OH (XVII),

in which R

7

is C

1

-C

10

alkyl, C

1

-C

10

alkyl substituted by halogen, CN, NO

2

, C

1

-C

5

alkoxy, C

1

-C

5

alkylthio, C

3

-C

6

alkenyloxy, C

1

-C

3

alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C

3

-C

10

alkenyl, C

3

-C

10

alkenyl substituted by halogen, C

1

-C

3

alkoxy or substituted or unsubstituted aryl or aryloxy, C

3

-C

5

alkynyl, C

3

-C

8

cycloalkyl, C

6

-C

12

bicycloalkyl, heterocyclyl or alicyclyl,

if appropriate in an inert solvent in the presence of an eqimolar amount of base.

Another process according to the invention for the preparation of the compounds of the formula I in which

R

1

is the group —OR

7

;

R

2

is a group R

88

R

89

N—,

and R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X— comprises a procedure in which

c

4

) a compound of the formula VI

in which R

7

is as defined under formula I and

R

3

is as defined above,

is reacted with an amine of the formula XIII, XIV or XV

R

88

R

89

NH (XIII),

in which R

20

, R

88

, R

89

, Y and n

7

are as defined under formula I,

if appropriate in a solvent; or

c

3

) the compound of the formula VI is first converted with a compound of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

is an aryl, phthalidyl, biphenyl or heteroaryl radical, and

X

1

is oxygen or sulfur,

in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V

in which R

3

is —X

1

—R

12

and

R

7

, R

12

and X

1

are as defined, and

d

4

) this is then reacted with an amine of the formula XIII, XIV or XV in a manner analogous to that described under C

4

); or in which

a

4

) 1,3,5-trichlorothiatriazine is converted with an alcoholate of the formula XVII

1

(R

7

—O

−

)

n

M

1

+n

(XVII

1

),

in which R

7

is as defined under formula I;

M

1

+n

is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and

n is 1, 2, 3 or 4,

in the presence of an inert organic solvent, into the compound of the formula VII

in which R

7

is as defined, and

b

4

) this is reacted with an amine of the formula XIII, XIV or XV

R

88

R

89

NH

in which R

20

, R

88

, R

89

, Y and n

7

are as defined under formula I,

if appropriate in a solvent, to give the compound of the formula VIII

in which R

2

and R

7

are as defined, and

c

5

) this is then reacted with a compound of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

is an aryl, phthalidyl, biphenyl or heteroaryl radical; and

X

1

is oxygen or sulfur,

in a solvent in the presence of a tertiary amine and, if appropriate, another base.

The process according to the invention for the preparation of the compounds of the formula I in which

R

1

is a group —NR

90

R

91

or an N-heterocyclic radical onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms;

R

2

is a group R

88

R

89

N—,

and R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—

comprises a procedure in which

e) a compound of the formula III

in which R

7

is as defined under formula I and

R

2

and R

3

are as defined,

is reacted with an amine of the formula XI or XII

in which R

90

and R

91

are as defined under formula I and

R

11

is a cyclic radical onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms,

if appropriate in a solvent; or in which

a

5

) 1,3,5-trichlorothiatriazine is converted with an amine of the formula XI or XII

in which R

90

and R

91

are as defined under formula I and

R

11

is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms,

or with an amide of the formula XI

1

or XII

1

,

in which R

90

, R

91

and R

11

are as defined;

M

2

+n

is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and

n is 1, 2, 3 or 4,

in the presence of an inert organic solvent and if appropriate a base, into the compound of the formula IX

in which R

1

is as defined, and

b

5

) this is reacted with an amine of the formula XIII, XIV or XV

in which R

20

, R

88

, R

89

, Y and n

7

are as defined under formula I,

if appropriate in a solvent, to give the compound of the formula X

in which R

1

and R

2

are as defined, and

c

6

) this is then reacted with a compound of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

is an aryl, phthalidyl, biphenyl or heteroaryl radical; and

X

1

is oxygen or sulfur,

in a solvent in the presence of a tertiary amine and a further equivalent amount of base.

Another process according to the invention for the preparation of compounds of the formula I in which

R

1

is a group —OR

7

;

R

2

is a group R

88

R

89

N—,

aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, comprises a procedure in which a compound of the formula I in which

R

1

is a group —OR

7

, in which

R

7

is other than in the end product; and

R

2

and R

3

are as defined

is reacted with an alcohol of the formula XVII

R

7

—OH (XVII)

in which R

7

is other than in the starting substance of the formula I, in the presence of an inert organic solvent and a catalytic or equimolar amount of base.

The abovementioned processes according to the invention for the preparation of compounds of the formula I follow equations 1 and 2, the scope of the compounds of the formula I being composed of the scopes of the compounds of the formulae II, III and IV shown in the equations mentioned.

In equation 1 the following applies:

a

1

) R

7

—OH (XVII), solvent, −60°-+80° C.;

a

2

) Bicycloalkyl epoxides,

solvent, 0°-130° C.;

a

3

) R

7

—OH (XVII), solvent, base, for example NaH, 10°-40° C.;

b

1

) R

14

—X

1

H (XXIII), solvent, base, for example NaH, −60°-+80° C.;

b

2

) R

12

—X

1

H (XVI), solvent, base, for example NaH, −60°-+50° C.;

b

3

) 2 mol R

12

—X

1

H (XVI), solvent, base, for example NaH, −60°-+50° C.;

c

2

) R

14

—X

1

H (XXIII), solvent, base, for example K tert-butylate, −60°-+80° C.;

c

3

) R

12

—X

1

H (XVI), solvent, base, for example NaH, −60°-+50° C.; and

d

3

) R

14

—X

1

H (XXIII), solvent, base, for example K tert-butylate, −60°-+80° C.;

a

4

) (R

7

—O

−

)

n

M

1

+n

(VII

1

), for example (R

7

—O

−

)(MgCl)

+

, solvent, for example tetrahydrofuran, −78°-0° C.;

b

4

) R

88

R

89

NH (XIII),

solvent, −78°-+40° C.;

a

5

) R

90

R

91

NH (XI) or

base, for example Et

3

N, solvent, or

(R

90

R

91

N

−

)

n

M

2

+n

(XI

1

) or

solvent, −78°-0° C.;

b

5

) R

88

R

89

NH (XIII),

solvent, −78°-+40° C.,

in which R

7

, R

11

, R

12

, R

13

, R

14

, R

20

, R

23

, R

88

, R

89

, R

90

, R

91

, n, n

7

, n

8

, n

11

, Y, X

1

, M

1

+n

and M

2

+n

are as defined above.

In equation 2, the following applies:

c

3

) R

12

—X

1

H (XVI), solvent, base, for example NaH, −60°-+50° C.;

c

4

) R

88

R

89

NH (XIII),

solvent, −50°-+50° C.;

d

4

) R

88

R

89

NH (XIII),

solvent, −20°-+100° C.;

e) R

90

R

91

NH (XI) or

solvent, 20°-150° C.;

c

5

) R

12

—X

1

H (XVI), solvent, tertiary amine, for example (CH

3

)

3

N, if appropriate base, for example NaOH, −10°-+70° C.;

c

6

) R

12

—X

1

H (XVI), solvent, tertiary amine, for example (CH

3

)

3

N, base, for example NaOH, −10°-+70° C.;

p) R

7

—OH (XVII), solvent, base

cat

, for example NaH, −60°-+50° C.; and

q) R

7

—OH (XVII), solvent, base, for example NaH, 0°-+50° C.;

in which R

7

, R

11

, R

12

, R

20

, R

88

, R

89

, R

90

, R

91

, Y, n

7

and X

1

are as defined above.

The substitution of the most reactive chlorine atom on the sulfur of the 1,3,5-trichloro-thiatriazine leads on the one hand by a process variant a

1

), by reaction with the alcohol of the formula XVII, by process variant a

2

), by reaction with bicycloalkyl epoxides or epoxides of the formula XVIII or XIX, or by process variant a

4

), by reaction with alcoholates of the formula XVII

1

, to the compounds of the formula VII, and on the other hand by process variant a

3

), by reaction with the alcohol of the formula XVII, directly to the compounds of the formula IV (equation 1).

Process variant a

2

) always gives 1-b-chloroalkoxy derivatives of the formula VII here.

The reaction according to process variant a

1

) is advantageously carried out in a non-polar organic solvent which is inert in the reaction, such as chlorinated hydrocarbons, for example methylene chloride, chloroform or carbon tetrachloride, aromatic hydrocarbons, for example benzene, toluene or xylenes, cyclic hydrocarbons, for example cyclohexane, or cyclic ethers, for example tetrahydrofuran or dioxane, at reaction temperatures of −60° C. to +80° C., preferably at temperatures of −30° C. to +50° C., if appropriate in the presence of an equimolar amount of base. Examples of suitable bases are organic bases, such as tertiary amines, for example trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo-[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene or alcoholates, for example potassium tert-butylate, sodium methylate or sodium ethylate. However, inorganic bases, such as hydrides, for example sodium or calcium hydride, hydroxides, such as sodium or potassium hydroxide, carbonates, such as sodium or potassium carbonate, or bicarbonates, such as potassium or sodium bicarbonate, can also be used as bases. In a preferred embodiment (Example H2), 2-chloroethanol and an equimolar amount of triethylamine are dissolved in carbon tetrachloride and a solution of 1,3,5-trichlorothiatriazine in carbon tetrachloride is added to this cooled solution (−15° C.), and the mixture is subsequently warmed to 0° C.

The reaction of 1,3,5-trichlorothiatriazine with bicycloalkyl epoxides or with epoxides of the formula XVIII or XIX is expediently carried out in the same solvents as listed under variant a

1

) at reaction temperatures of 0° to 130° C., preferably at reaction temperatures of 25° to 80° C.

In a preferred embodiment (Example H1), 1,3,5-trichlorothiatriazine is dissolved in carbon tetrachloride and an equimolar amount of cyclohexene oxide is added at room temperature.

In process variant a

4

), 1,3,5-trichlorothiatriazine is reacted with an alcoholate of the formula XVII

1

(R

7

—O

−

)

n

M

1

+n

(XVII

1

),

in which R

7

is as defined under formula I;

M

1

+n

is a mono- or polyvalent metal ion, for example an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table, preferably lithium, magnesium, zinc, aluminium, silicon, fin or titanium, but especially preferably magnesium; and n is the number 1, 2, 3 or 4 (=oxidation number of the corresponding metal ion) in the presence of an inert organic solvent, such as ethers, for example diethyl ether or tetrahydrofuran (THF).

In the compounds of the formula XVII

1

in the case of polyvalent metal ions M

1

+n

, if n>1, further substituents, for example halogen, C

1

-C

4

alkyl or cyano, are also possible in addition to one or more R

7

—O

−

groups. Furthermore, the alcoholates of the formula XVII

1

can also be employed in combination With salts, for example aluminium, tin or zinc chloride or aluminium or zinc bromide.

The reaction temperatures for this reaction range from −70° to +20° C., but are preferably below 0° C.

The resulting compound of the formula VII can be isolated, if appropriate, or else used directly for the next reaction stage.

In process variant a

3

), the most reactive chlorine atom on the sulfur of the thiatriazine ring is replaced in particular by the group —OR

7

with addition of an equimolar amount of base; the less reactive chlorine atoms on the carbon atoms in the 3- and 5-positions can also be partly or completely replaced by the group —OR

7

, depending on the reaction conditions (for example low reaction temperatures; slow warming of the reaction mixture).

The replacement according to variant a

3

) is advantageously carried out in the presence of a non-polar organic solvent which is inert in the reaction. Such solvents are listed under variants a

1

) and a

2

). The alcohol of the formula XVII is accordingly converted into the corresponding alcoholate in the solvent by treatment with a strong base, such as metal hydrides, for example sodium hydride, and this alcoholate solution is added dropwise to a solution of 1,3,5-trichlorothiatriazine at temperatures of 10° to 40° C., in particular at temperatures of 20° to 30° C., while cooling.

In a preferred embodiment (Example H9), the 1,3,5-trichlorothiatriazine is dissolved in tetrahydrofuran and a methanolic sodium methylate solution in tetrahydrofuran is added dropwise at 30° C., while cooling. Completely substituted 1,3,5-trimethoxythiatriazine is obtained.

Preparation of the thiatriazine derivatives of the formula VI (equation 1) according to process variant b

2

) is advantageously carried out by reaction of the corresponding 3,5-dichloro-thiatriazine of the formula VII with an alcohol of the formula XVI

R

12

—X

1

H (XVI),

in which R

12

and X

1

are as defined,

in the presence of an organic solvent which is inert in the reaction, such as cyclic ethers, for example tetrahydrofuran or dioxane, and an equimolar amount of base, for example alkali metal hydrides, preferably sodium or lithium hydride, or alcoholates, for example potassium tert-butylate. The reaction temperatures range from −60° to +50° C., preferably from +40° to −10° C.

In a preferred embodiment (Example H4), ethyl salicylate is dissolved in tetrahydrofuran together with the equimolar amount of sodium hydride, 1-chloroethoxy-3,5-dichlorothiatriazine is added dropwise at −30° C. and the mixture is then warmed to room temperature.

The substitution of the remaining chlorine atom in the thiatriazine derivative of the formula VI with a further radical —X

1

R

12

is carried out in accordance with process variant c

3

). This reaction advantageously proceeds analogously to variant b

2

), and leads to symmetrically or asymmetrically substituted thiatriazine derivatives of the formula V, depending on the compound of the formula XVI employed (equation 1).

The thiatriazine derivatives of the formula V can also be prepared directly from the compounds of the formula VII according to process variant b

3

), and leads exclusively to symmetrically substituted derivatives being formed. The reaction according to process variant b

3

) is advantageously carried out analogously to process variant b

2

) or c

3

), but with the difference that two molar equivalents of the compound of the formula XVI and accordingly two molar equivalents of base are employed.

The preparation of the thiatriazine derivatives of the formula IV (equation 1), in which R

2

, R

3

and R

7

are as defined,

is advantageously carried out in accordance with process variant d

3

) from the thiatriazine derivatives of the formula V by reaction with alcohols or thiols of the formula XXIII

R

14

—X

1

H (XXIII),

in which R

14

and X

1

are as defined,

in an inert organic solvent analogously to process variant a

1

) at temperatures of −60° to +80° C., preferably −50° C. to room temperature, in the presence of an equimolar amount of base. Suitable bases are, for example, organic bases, such as tertiary amines, for example triethylamine, alcoholates, for example potassium tert-butylate, or inorganic bases, such as alkali metal hydrides, for example sodium or lithium hydride. If appropriate, the alcohol of the formula XXIII can also be used as the solvent. Partial or complete exchange can take place both on the sulfur atom (1-position) and on the carbon atoms in the 3- and 5-positions, depending on the reaction conditions (reaction temperature, reaction time) and the ease of substitution of the substituents in the starting compound of the formula V. In a preferred embodiment (Example H10), 1-(b-chloroethoxy)-3,5-di(2′,5′-difluorophenoxy)-thiatriazine is dissolved in methanol and a sodium methylate solution in methanol is added dropwise at low temperatures (−60° C.). The derivative substituted by methoxy in the 1-position is first formed by this procedure and is converted into 1,3-dimethoxy-5-(2′,5′-di-fluorophenoxy)thiatriazine when the reaction solution is warmed.

In another preferred embodiment (Example H11), 1-(b-chloroethoxy)-3,5-di(2′,4′-dichlorophenoxy)thiatriazine is dissolved in tetrahydrofuran and a solution of 2,2,2-trichloroethanol and sodium hydride is added dropwise at low temperatures (−50° C.). After the reaction mixture has been warmed up, the derivative of the formula IV substituted by 2,2,2-trichloroethoxy in the 3- and 5-positions on the thiatriazine ring is isolated.

The reactions according to process variants b

1

) and c

2

) (equation 1) starting from the thiatriazine intermediates of the formulae VII and VI also give thiatriazines of the formula IV. Both variants b

1

) and c

2

) are advantageously carried out analogously to process variant d

3

) by reaction of the thiatriazine intermediates of the formula VII or VI with alcohols or thiols of the formula XXIII in organic solvents which are inert in the reaction at reaction temperatures of −60° to +80° C.

In these two process variants b

1

) and c

2

) also, partial or complete exchange of the substituents in the 1-, 3- and 5-positions can be obtained, depending on the reactivity of the substituents in the 1-, 3- and 5-positions of the thiatriazine intermediates of the formulae VII and VI and on the reaction conditions, for example the use of an equimolar amount of alcohol or thiol of the formula XXIII and an equimolar or catalytic amount of base.

In an embodiment preferred for variant b

1

) (Example H12), 1-(b-chloroethoxy)-3,5-di-chlorothiatriazine is dissolved in tetrahydrofuran and a solution of 3 molar equivalents of tert-butylmercaptan and triethylamine in tetrahydrofuran is added dropwise at low temperatures (−50° C.). After the reaction mixture has been warmed up to 0° C., a 4/1 product mixture comprising 1-(b-chloroethoxy)-3-chloro-5-tert-butylmercaptothiatriazine and 1-(b-chloroethoxy)-3,5-di-tert-butylmercaptothiatriazine is obtained.

The preparation of the thiatriazine derivatives of the formula VIII (equation 1) according to process variant b

4

) is advantageously carried out by reaction of the 3,5-dichlorothiatriazine of the formula VII with an amine of the formula XIII, XIV or XV, if appropriate in the presence of a solvent, preferably tetrahydrofuran or acetonitrile, if appropriate mixed with water, at reaction temperatures of −78° to +40° C.

In a preferred embodiment (Example H20), 3,5-dichloro-1-(3-hexyloxy)thiatriazine is reacted with ammonia in tetrahydrofuran at 0° C.

In process variant a

5

) in equation 1, the most reactive chlorine atom on the sulfur atom of the trichlorothiatriazine is substituted by addition of an amine of the formula XI or XII in an inert organic solvent and if appropriate in the presence of a base, for example a tertiary amine, for example triethylamine. Suitable solvents for this substitution are ethers, for example tetrahydrofuran, at reaction temperatures of −78° to +25° C., but preferably at reaction temperatures below −40° C.

Alternatively, instead of the amines of the formula XI or XII, the amides of the formula XI

1

or XII

1

(R

90

R

91

N

−

)

n

M

2

+n

(XI

1

) or

in which R

90

and R

91

are as defined under formula I;

R

11

is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms;

M

2

+n

is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and

n is the number 1, 2, 3 or 4 (=oxidation number of the corresponding metal ion), can be reacted with the 1,3,5-trichlorothiatriazine in an organic solvent, for example an ether, for example diethyl ether or, preferably tetrahydrofuran.

The reaction temperatures range from −78° to 0° C., but are preferably below −40° C. In the compounds of the formula XI

1

or XII

1

, in the case of polyvalent metal ions M

2

+n if n>

1, further substituents, for example halogen or C

1

-C

4

alkyl, are also possible in addition to one or more amide groups.

The compound of the formula IX can be isolated, if appropriate, or else used directly for the next reaction stage (b

5

)).

In a preferred embodiment (Example H21), a mixture comprising equimolar amounts of octahydroindole and triethylamine is added dropwise to 1,3,5-trichlorothiatriazine in diethyl ether at −70° to −60° C.

Further reaction of the thiatriazine of the formula IX in accordance with process variant b

5

) in equation 1 gives the thiatriazine of the formula X. This process variant is advantageously carried out analogously to process variant b

4

).

In a preferred embodiment (Example H23), an aqueous ammonia solution is added to 3,5-dichloro-1-(octahydroindol-1-yl)thiatriazine in tetrahydrofuran.

In another preferred embodiment (Example H22), a suspension of piperidine and n-butyllithium is added dropwise to a solution of trichlorothiatriazine in tetrahydrofuran which has been cooled to −60° C., and the mixture is subsequently treated further with ammonia gas at −10° C. until the conversion is complete.

In the reactions according to process variants p) and q) (equation 2), only the substituent in the 1-position, i.e. on the sulfur atom of the thiatriazine ring, is substituted selectively.

The thiatriazine derivatives of the formula III can be obtained either by reaction of the 3-chlorothiatriazine derivatives of the formula VI with the amines of the formula XIII, XIV or XV in accordance with process variant c

4

), or by reaction of the 5-chlorothiatriazine derivatives of the formula VIII with an alcohol of the formula XVI in accordance with process variant c

5

) (equation 2).

The substitution reaction according to variant c

4

) can advantageously be carried out in an inert organic solvent, such as a cyclic ether, for example tetrahydrofuran or dioxane, at temperatures of −50° to +50° C., preferably at temperatures of −20° to +20° C.

In a preferred embodiment (Example H15), 3-chloro-1-(b-chloroethoxy)-5-(2′-carboethoxyphenoxy)thiatriazine is dissolved in tetrahydrofuran, and dimethylamine is passed in at 0° C. until conversion is complete.

The substitution reaction according to variant c

5

) can advantageously be carried out in an organic solvent, such as an ether, for example tetrahydrofuran, or a halogenated hydrocarbon, for example methylene chloride, to which water is admixed, if appropriate, in the presence of a catalytic to excess amount of a tertiary amine, for example trimethylamine, and in the presence or absence of a further base, for example sodium hydroxide, at temperatures from −10° to +70° C., preferably at 0° to 25° C.

In a preferred embodiment (Example H16), a mixture of 3-amino-5-chloro-1-(3-hexyloxy)thiatriazine, difluorophenol and trimethylamine in methylene chloride is allowed to react at 20° C.

Another possibility for the preparation of the thiatriazines of the formula III starts from the thiatriazine intermediates of the formula V, one of the radicals —X

1

R

12

being substituted by amines of the formula XIII, XIV or XV according to process variant d

4

) (equation 2). This substitution reaction is advantageously carried out analogously to variant c

4

) in an inert organic solvent at temperatures from −20° to +100° C., preferably at 0° to 50° C.

According to process variant e), in equation 2, the group —OR

7

bonded to the sulfur of the thiatriazine ring of the formula III can be substituted selectively by an amino group. As a result, compounds of the formula II in which

R

1

is a group —NR

90

R

91

or an N-heterocyclic radical, are obtained. This reaction is advantageously carried out with amines of the formula XI or XII in an inert organic solvent, such as an aromatic hydrocarbon, for example toluene or xylenes, at temperatures of 20° to 150° C., preferably at temperatures of 50° to 100° C.

In a preferred embodiment (Example H18), 1-(2′-chlorocyclohexanolyl)-3-amino-5-(2′,6′-difluorophenoxy)thiatriazine is heated at 80°-90° C. together with decahydroquinoline in toluene until conversion is complete.

Another possibility for the preparation of the thiatriazines of the formula II starts from the 1,3-disubstituted 5-chlorothiatriazines of the formula X, the 5-chlorine atom being replaced by alcohols of the formula XVI according to process variant c

6

) in equation 2. This replacement is advantageously carried out in the presence of a catalytic to excess amount of a tertiary amine, for example trimethylamine, and a further equivalent amount of base, for example sodium hydroxide, in an organic solvent, such as an ether, for example tetrahydrofuran, or a halogenated hydrocarbon, for example methylene chloride, to which water is admixed if appropriate. The reaction temperatures are −10° to +70° C., preferably 0° to 25° C.

In a preferred embodiment (Example H19), 3-amino-5-chloro-1-(piperidin-1-yl)thiatriazine and pentafluorophenol are brought together in methylene chloride with 2N sodium hydroxide solution and aqueous trimethylamine and allowed to react. In the thiatriazine derivatives of the formulae V and III, the group —OR

7

bonded to the sulfur can be substituted selectively by another alcohol of the formula XVII

R

7

—OH (XVII),

in which R

7

is as defined under formula I, according to process variants p) and q) in equation 2.

Other compounds of the formulae V and III and of the formula I can be prepared in this way and by customary derivatzation.

In the case of the compounds of the formula V, this exchange is advantageously carried out according to process variant p) with an excess of alcohol, but at least the equimolar amount of alcohol, in an inert organic solvent, such as a cyclic ether, for example tetrahydrofuran or dioxane, at temperatures from −60° to +50° C., preferably at temperatures from −40° to +10° C., in the presence of a catalytic amount of base, for example 1-30 mol %, preferably 5-20 mol %. Suitable bases are, for example, metal hydrides, such as sodium hydride, or alcoholates, such as potassium tert-butylate.

The exchange of the group —OR

7

in the case of the compounds of the formula III in accordance with process variant q) can be carried out analogously to process variant p), with the difference that reaction temperatures of 0° to 50° C., preferably 10° to 30° C., are used and that the amount of base used for the exchange reaction is less critical. Equimolar amounts of bases are preferably used.

In a preferred embodiment (Example H14), isopropanol and sodium hydride are initially introduced into tetrahydrofuran and 3-amino-1-(b-chloroethoxy)-5-(2′,5′-difluorophenoxy)thiatriazine is added to this suspension at room temperature.

The thiatriazines of the formula I or of the formulae II, III and IV, in which

R

2

and/or R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and

X is sulfur,

obtained in the process variants described above can subsequently be oxidized to give the corresponding sulfoxides and sulfone derivatives of the formula I or of the formulae II, III and IV, in which

R

2

and/or R

3

is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and

X is —SO— or —SO

2

—,

analogously to known standard processes, for example with hydrogen peroxide or m-chloroperbenzoic acid. In order to avoid undesirable side reactions, the conditions for this oxidation must be evaluated in respect of the reactivities of the other substituents on the thiatriazine ring. Examples of such sulfur oxidations are described in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume IV, Georg Thieme Verlag Stuttgart.

The present processes according to the invention have the following advantages:

1. Easy accessibility of the 1,3,5-trichlorothiatriazine and of the other starting compounds of the formulae XVII, XVIII, XIX, XVI, XXIII, XI, XII, XIII, XIV and XV, and of the bicycloalkyl epoxides from the scope of formula I;

2. Low number of synthesis stages;

3. Selectivity of the exchange reactions on the thiatriazine ring;

4. Wide possibilities for derivatization in respect of the choice of substituents R

1

, R

2

and R

3

on the thiatriazine ring and associated wide possibilities of variation for the thiatriazines of the formula I; and

5. Exchange reactions are carried out under mild reaction conditions (for example low temperatures) and are compatible for a large number of functional groups.

The thiatriazine derivatives of the formulae V, VI, VII, VII, IX and X are novel. They are important intermediates for the synthesis of the compounds of the formula 1. The invention therefore also relates to these novel compounds and processes for their preparation, and to the use of the compounds of the formulae V, VI, VII, VIII, IX and X for the preparation of compounds of the formula I, excluding the compounds

wherein R

01

is hydrogen, methyl, ethyl, n-propyl, i-butyl or cyclohexyl; and R

02

and R

03

are ethyl or benzyl.

For the intermediates of the formulae V, VI, VII, VIII, IX and X, the same preferences apply in respect of R

3

and R

7

as for the compounds of the formula I.

The starting compounds of the formulae XVII, XVIII and XIX required in process variants a

1

), a

2

), a

3

), p) and q) and the corresponding bicycloalkyl epoxides from the scope of formula I either are obtainable commercially or can be prepared by generally known methods. The preparation of such compounds is described, for example, in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume VI and VI/3, Georg Thieme Verlag Stuttgart.

The starting compounds of the formulae XVI and XXIII required in process variants b

1

), b

2

), b

3

), c

2

), c

3

) and d

3

) either are obtainable commercially or can be prepared by generally known methods. The preparation of such compounds is described, for example, in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume VI and IX, Georg Thieme Verlag Stuttgart.

The amines of the formulae XI, XII, XIII, XIV and XV required in process variants c

4

), d

4

) and e) either are obtainable commercially or can be prepared analogously to known standard processes. The preparation of such compounds is described, for example, in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume XI, Georg Thieme Verlag Stuttgart.

The alcoholates of the formula XVII

1

required in process variant a

4

) can be prepared analogously to known standard processes, for example by reaction of the corresponding alcohol of the formula XVII with an M

1

-organometallic compound, for example C

1

-C

4

alkyllithium or C

1

-C

8

alkylmagnesium halide, or by reaction with an M

1

-metal compound which contains at least one leaving group, for example cyano or, preferably, halogen, and if appropriate one or more C

1

-C

4

alkyl groups, in the presence of a base. The compounds of the formula XVII

1

do not have to be isolated in a pure form, but can be further used directly.

The amides of the formulae XI

1

and XII

1

required in process variant a

5

) can be prepared analogously to known standard processes, for example by reaction of the corresponding amines of the formula XI and XII with an M

2

-organometallic compound, for example C

1

-C

4

alkyllithium or C

1

-C

8

alkylmagnesium halide, or by reaction with an M

2

-metal compound which has at least one leaving group, for example halogen, and where appropriate one or more C

1

-C

4

alkyl groups, in the presence of a base.

The preparation of the starting compound 1,3,5-trichlorothiatriazine is described in DD-A-113 006 (Example 1).

The resulting compounds of the formula I can be isolated in the customary manner by concentration or evaporation of the solvent, and purified by recrystallization or trituraaon of the solid residue in solvents in which they do not dissolve readily, such as ethers or aliphatic hydrocarbons, by distillation or by means of column chromatography with a suitable eluting agent.

If no controlled synthesis is carried out for isolation of pure isomers or diastereomers, the product can be obtained as a mixture of two or more isomers or diastereomers. The isomers or diastereomers can be separated by methods known per se. If desired, for example, pure optically active isomers or diastereomers can also be prepared by synthesis from corresponding optically active starting materials, for example cis- or trans-decalin, cis- or trans-2,6-dimethylmorpholine or cis- or trans-decahydro(iso)quinoline.

The end products of the formula I can be isolated in the customary manner by concentration and/or evaporation of the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they do not dissolve readily, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

For use according to the invention of the compounds of the formula I, including the compounds of the formulae I

1

to I

7

, or compositions comprising these, all the methods of application customary in agriculture, for example preemergence and postemergence application, as well as various methods and techniques such as, for example, controlled release of the active compound, are suitable. For this, the active compound is adsorbed in solution onto mineral granule carriers or polymerized granules (urea/formaldehyde) and the granules are dried. If appropriate, a coating can additionally be applied (coated granules), allowing the active compound to be released in a metered form over a certain period of time.

The compounds of the formula I, including the compounds of the formulae I

1

to I

7

, can be employed in unchanged form, i.e. as they are obtained in the synthesis, but they are preferably processed in the customary manner with the auxiliaries customary in formulation technology, for example to give emulsifiable concentrates, solutions which can be sprayed or diluted directly, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. The methods of application, such as spraying, atomizing, dusting, wetting, scattering or pouring, like the nature of the compositions, are chosen according to the required aims and the given circumstances.

The formulations, i.e. the compositions, formulations, preparations, combinations or mixtures comprising the active compound of the formula I or at least one active compound of the formula I, including the compounds of the formulae I

1

to I

7

and as a rule one or more solid or liquid formulation auxiliaries, are prepared in a known manner, for example by intimate mixing and/or grinding of the active compounds with the formulation auxiliaries, for example solvents or solid carriers. Surface-active compounds (surfactants) can, furthermore, additionally be used in the preparation of the formulations.

Solvents can be: aromatic hydrocarbons, preferably fractions C

8

to C

12

, for example xylene mixtures or substituted naphthalenes phthalic acid esters, such as dibutyl or dioctylphthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols, and ethers and esters thereof, such as ethanol, ethylene glycol or ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethylformamide, and epoxidized or non-epoxidized vegetable oils, such as epoxidized coconut oil or soya oil; or water.

Solid carriers, for example for dusts and dispersable powders, which are used are as a rule natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acid or highly disperse absorbent polymers can also be added to improve the physical properties of the formulation. Granular adsorptive carriers for granules are porous types, for example pumice, crushed brick, sepiolite or bentonite, and non-sorbent carrier materials are, for example, calcite or sand. A large number of pregranulated materials of inorganic or organic nature, such as, in particular, dolomite or comminuted plant residues, can moreover be used.

Surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties, depending on the nature of the active compound of the formula I to be formulated

Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

Soaps are the alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acids (C

10

-C

22

), for example the Na or K salts of oleic or stearic acid, or of naturally occurring fatty acid mixtures, which can be obtained, for example, from coconut oil or tallow oil. They are also the fatty acid methyl-taurine salts.

However, so-called synthetic surfactants are more frequently used, in particular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty alcohol sulfonates or sulfates are as a rule in the form of alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and contain an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals, for example the Na or Ca salt of ligninsulfonic acid, of dodecyl-sulfuric acid ester or of a fatty alcohol sulfate mixture prepared from naturally occurring fatty acids. These also include the salts of the sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having 8-22 C atoms. Alkylarylsulfonates are, for example, the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutyinaphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product.

Salts can furthermore also be corresponding phosphates, for example salts of the phosphoric acid ester of a p-nonylphenol-(4-14)-ethylene oxide adduct, or phospholipids.

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

Other suitable nonionic surfactants are the water-soluble adducts, containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups, of polyethylene oxide on polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Examples of nonionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ether, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, can also be used.

The cationic surfactants are, in particular, quaternary ammonium salts, which contain at least one alkyl radical having 8 to 22 C atoms as N substituents and lower, halogenated or non-halogenated alkyl, benzyl) or lower hydroxyalkyl radicals as further substituents. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethyl ammonium bromide.

The surfactants customary in formulation technology which can also be used in the compositions according to the invention are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual”, MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant Handbook], Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Volume I-III, Chemical Publishing Co., New York, 1980-81.

The herbicidal formulations as a rule comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.

While concentrated compositions are more preferable as commercial goods, the end user as a rule uses dilute compositions.

The compositions can also comprise further additives, such as stabilizers, for example epoxidized or nonepoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active compounds.

In particular, preferred formulations have the following composition:

(%=per cent by weight)

Emulsifiable Concentrates:

Active compound: 1 to 90%, preferably 5 to 50%

Surface-active agent: 5 to 30%, preferably 10 to 20%

Solvent: 15 to 94%, preferably 70 to 85%

Dusts:

Active compound: 0.1 to 50%, preferably 0.1 to 1%

Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension Concentrates:

Active compound: 5 to 75%, preferably 10 to 50%

Water: 94 to 24%, preferably 88 to 30%

Surface-active agent: 1 to 40%, preferably 2 to 30%

Wettable Powders:

Active compound: 0.5 to 90%, preferably 1 to 80%

Surface-active agent: 0.5 to 20%, preferably 1 to 15%

Solid carrier material: 5 to 95%, preferably 15 to 90%

Granules:

Active compound: 0.1 to 30%, preferably 0.1 to 15%.

Solid carrier: 99.5 to 70%, preferably 97 to 85%

The active compounds of the formula I, including the compounds of the formulae I

1

to I

7

, are as a rule successfully employed on the plants or their environment with rates of application of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired action can be determined by experiments. It depends on the mode of action, the stage of development of the crop plant and the weed and on the application (location, time, method), and can vary within relatively wide limits as a result of these parameters.

The compounds of the formula I, including the compounds of the formulae I

1

to I

7

, have herbicidal and growth-inhibiting properties which enable them to be used in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, oilseed rape, maize and rice.

Crops are also to be understood as those which have been rendered tolerant to herbicides or classes of herbicide by conventional breeding or genetic engineering methods.

The weeds to be controlled can be both monocotyledon and dicotyledon weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, lpomoea, Chrysanthemum, Galium, Viola and Veronica.

The following examples illustrate the invention further, without limiting it.

PREPARATION EXAMPLES

Example H1

Preparation of 1-(trans-2-chlorocyclohexyloxy)-3,5-dichlorothiatriazine (process a

2

)

5.11 g (0.025 mol) of 1,3,5-trichlorothiatriazine are dissolved in 50 ml of carbon tetrachloride, and 2.94 g (0.03 mol) of cyclohexene oxide are added at 25° C. The weakly exothermic reaction is carried out at 25-35° C. and has ended after 30 minutes. The cloudy solution formed is filtered and the filtrate is concentrated. 8.7 g of crude product are obtained as a residue, recrystallization of which from a mixture of ethyl acetate and hexane gives 6.75 g (89% of theory) of the desired product of melting point 82-83° C.

Example H2

Preparation of 1-(2-chloroethoxy)-3,5-dichlorothiatriazine (process a

1

)

0.80 g (0.01 mol) of 2-chloroethanol and 1.21 g (0.012 mol) of triethylamine are dissolved in 30 ml of carbon tetrachloride and the solution is cooled to −15° C. Thereafter, a solution of 2.04 g (0.01 mol) of 1,3,5-trichlorothiatriazine in 5 ml of carbon tetrachloride is added dropwise at this temperature and the temperature is then allowed to rise to 0° C. The triethylamine hydrochloride is filtered off and the filtrate is concentrated to give 1.85 g of crude product. Recrystallization from 10 ml of hexane gives 1.65 g (67% of theory) of the desired product of melting point 54-55° C.

Example H3

Preparation of 1-methoxy-3,5-dichlorothiatriazine (process a

1

)

4.09 g (0.02 mol) of 1,3,5-trichlorothiatriazine are stirred as a suspension in 50 ml of carbon tetrachloride at −25° C., and a solution of 0.70 g (0.022 mol) of methanol in a little carbon tetrachloride is added dropwise. During this operation, the trichlorothiatriazine dissolves apart from a little insoluble product. The mixture is then warmed to 0° C. and filtered and the filtrate is concentrated on a rotary evaporator at a maximum of 50° C. 3.25 g of the desired product, which, according to the

13

C-NMR spectrum and thin layer chromatogram (silica gel; eluting agent ethyl acetate/hexane 1/3), contains practically no further impurities, are obtained as the residue. The compound is unstable and decomposes within a few hours when left to stand.

The compounds listed in the following Table I can be prepared analogously to Examples H1 to H3.

TABLE 1

Compounds of the formula VII

(VII)

Comp.

No.

R

7

Process

Physical data

1.1

—CH

3

a

1

13

C-NMR: 167.5 ppm; 52.6 ppm

1.2

—C

2

H

5

1.3

—C

5

H

11

(n)

1.4

—C

10

H

21

(n)

1.5

—CH(CH

3

)

2

1.6

—CH

2

CH(CH

3

)

2

1.7

—CH

2

CH

2

Cl

a

1

Melting point 54-55° C.

1.8

—CH

2

CHBrCH

2

Br

1.9

—CH

2

CH

2

F

1.10

—CH

2

CH

2

(CF

2

)

3

CF

3

1.11

1.12

—CH

2

CHCl

2

a

1

13

C-NMR: 167.7 ppm; 71.1 ppm;

68.6 ppm

1.13

—CH(CH

3

)(CH

2

)

5

CH

3

1.14

1.15

a

2

Melting point 82-83° C.

1.16

1.17

1.18

1.19

a

2

13

C-NMR: 166.8 ppm; 88.9 ppm; 64.5 ppm; 33.1 ppm; 31.2 ppm; 25.7 ppm; 25.3 ppm; 25.1 ppm; 24.1 ppm

1.20

a

1

13

C-NMR: 166.5 ppm; 82.8 ppm; 33.4 ppm; 25.2 ppm; 23.4 ppm:

1.21

a

2

13

C-NMR: 167.2 ppm; 88.6 ppm; 62.5 ppm; 33.2 ppm; 30.8 ppm; 21.0 ppm

1.22

a

1

13

C-NMR: 166.5 ppm; 85.9 ppm; 33.2 ppm; 26.8 ppm; 22.5 ppm

1.23

1.24

1.25

1.26

1.27

a

2

13

C-NMR: 167.5 ppm; 136.0 ppm; 129.6 ppm; 129.2 ppm; 128.9 ppm; 127.5 ppm

1.28

1.29

1.30

1.31

—CH

2

CH

2

SC

2

H

5

1.32

—CH(CH

3

)C

6

F

5

1.33

1.34

—CH

2

C≡CH

a

1

13

C-NMR: 167.7 ppm; 79.0 ppm;

75.3 ppm; 55.5 ppm

1.35

1.36

1.37

1.38

1.39

1.40

—CH

2

CH

2

COOC

2

H

5

1.41

1.42

1.43

1.44

—CH

2

CH═CH

2

1.45

1.46

1.47

1.48

1.49

1.50

1.51

a

2

13

C-NMR: 167.0 ppm; 166.8 ppm; 84.3 ppm; 45.7 ppm; 26.4 ppm; 9.5 ppm

1.52

—CH

2

CH

2

OCH

3

1.53

—CH

2

CH

2

Br

1.54

a

2

1

H-NMR: 3.9-4.1 ppm (3 H); 1.6-2.0 ppm (2 H); 1.05 ppm (3 H)

1.55

1.56

1.57

1.58

1.59

1.60

1.61

1.62

1.63

1.64

1.65

1.66

1.67

1.68

1.69

1.70

1.71

1.72

1.73

1.74

1.75

1.76

1.77

a

2

Melting point 67-68° C.

1.78

1.79

1.80

1.81

1.82

1.83

—(CH

2

)

7

CH

3

1.84

1.85

a

2

1

H-NMR: 8.2 ppm (2 H); 7.6 ppm (1 H); 7.5 ppm (2 H); 4.85 ppm (1 H); 4.6 ppm (1 H); 4.4 ppm (1 H); 3.7 ppm (2 H)

1.86

—CH(CH

2

Cl)

2

1.87

1.88

—CH

2

-adamantyl

1.89

1.90

1.91

—CH

2

CH

2

CN

1.92

1.93

1.94

1.95

1.96

a

2

Oil

1.97

1.98

1.99

1.100

—CH

2

CH

2

CH(C

2

H

5

)

2

1.101

—CH(C

2

H

5

)

2

1.102

—CH

2

CH(CH

3

)Cl

1.103

1.104

1.105

1.106

1.107

1.108

1.109

1.110

1.111

1.112

1.113

1.114

1.115

—CH

2

C

6

F

5

1.116

1.117

—CH

2

CH

2

Si(CH

3

)

3

1.118

1.119

1.120

1.121

1.122

1.123

1.124

1.125

—CH

2

CH

2

OCOCH

3

1.126

1.127

1.128

1.129

1.130

1.131

1.132

1.133

1.134

1.135

1.136

1.137

Example H4

Preparation of 1-chloroethoxy-2-chloro-3-(2′-carboethoxyphenoxy)thiatriazine

3.32 g (0.02 mol) of ethyl salicylate are stirred with 0.96 9 of 55% sodium hydride (0.022 mol) in 50 ml of tetrahydrofuran under nitrogen. With evolution of hydrogen, a clear solution forms, which is added dropwise to a solution of 4.97 g (0.02 mol) of 1-chloroethoxy-3,5-dichlorothiatriazine at −30° C. The mixture is warmed to room temperature and extracted with water and ethyl acetate at pH 6, with addition of a little acetic acid. After the solvent has been evaporated, 7.2 g of crude product are obtained, which is chromatographed on silica gel with a mixture of ethyl acetate and hexane 3/7. The desired product is obtained as an oil in a yield of 6.6 g (95% of theory).

The compounds listed in the following Table 2 can be prepared analogously to Example H4.

TABLE 2

Compounds of the formula VI

(VI)

Comp.

No.

R

7

R

3

Physical Data

2.1

—C

5

H

11

(n)

2.2

—CH

2

CHCl

2

—SC

6

Cl

5

Melting point 128-129° C.

2.3

2.4

—CH

2

CH

2

Cl

1

H-NMR: 7.2-8.1 ppm (4 H); 3.6-4.4 ppm (6 H); 1.4 ppm (3 H)

2.5

2.6

2.7

—OC

6

F

5

2.8

—CH

2

CH

2

Cl

13

C-NMR: 169.8 ppm; 166.5 ppm; 150.9 ppm; 129.7 ppm; 126.7 ppm; 121.5 ppm; 66.1 ppm; 41.4 ppm

2.9

—CH

2

C≡CH

2.10

13

C-NMR: 169.2 ppm; 164.8 ppm; 139-148 ppm; 103.7 ppm; 84.5 ppm

2.11

—OC

6

F

5

2.12

2.13

13

C-NMR: 168.9 ppm; 165.2 ppm; 155.7 ppm; 145.7 ppm; 125.4 ppm; 122.7 ppm; 81.4 ppm; 33.4 ppm; 24.8 ppm; 23.5 ppm

2.14

—CH

2

CH

2

OCH

3

2.15

2.16

—CH

2

CH═CH

2

2.17

2.18

13

C-NMR: 169.7 ppm; 167.0 ppm; 118.6-148.6 ppm; 70.0 ppm; 59.5 ppm

2.19

2.20

2.21

2.22

2.23

—SC

6

F

5

2.24

13

C-NMR: 169.7 ppm; 166.4 ppm; 152.1 ppm; 151.6 ppm; 130.0 ppm; 110.6 ppm; 108.8 ppm; 105.0 ppm

2.25

2.26

2.27

2.28

2.29

—CH

2

COOC

2

H

5

2.30

1

H-NMR: 6.9-7.3 ppm (4 H); 4.4 ppm (1 H); 4.0 ppm (1 H); 3.8 ppm (3 H); 1.2-2.2 ppm (12 H)

2.31

—CH(CH

3

)

2

2.32

—CH

2

CH

2

Cl

—SC

6

F

5

Melting point 72-73° C.

2.33

—CH

2

CH

2

Cl

2.34

—CH

2

CH

2

Cl

2.35

—CH

2

CH

2

Cl

2.36

—CH

2

CH

2

Cl

2.37

—CH

2

CH

2

Cl

2.38

—CH

2

CH

2

Cl

2.39

—CH

2

CH

2

Cl

2.40

—CH

2

CH

2

Cl

2.41

—OC

6

F

5

2.42

2.43

2.44

—OC

6

F

5

2.45

—OC

6

F

5

2.46

—SC

6

F

5

2.47

—CH

2

CH

2

Cl

2.48

—CH

2

CH

2

Cl

2.49

—CH

2

CH

2

Cl

1

H-NMR: 7.5-7.8 ppm (3 H); 5.55 ppm (1 H); 4.2 ppm (1 H); 3.9 ppm (1 H); 3.15 ppm (2 H); 1.6 ppm (3 H)

2.50

—CH

3

2.51

—CH(CH

3

)

2

2.52

—CH

2

CH

2

F

2.53

2.54

—CH

2

CH

2

Cl

2.55

—CH

2

CH

2

Cl

2.56

—CH

2

CH

2

Cl

2.57

—CH

2

CH

2

Cl

2.58

2.59

—CH

2

CH

2

Br

2.60

—CH

2

CH

2

Cl

2.61

—CH

2

CH

2

Cl

2.62

2.63

—CH

2

CH

2

Cl

2.64

—CH

2

CH

2

Cl

2.65

2.66

2.67

—CH

2

CH

2

Br

C

6

F

5

S—

2.68

—CH

2

CH

2

Cl

2.69

—CH

2

CH

2

Cl

2.70

—CH

2

CH

2

Cl

2.71

—CH

2

CH

2

Cl

2.72

—CH

2

CH

2

Cl

2.73

—CH

2

CH

2

F

2.74

—CH

2

CH

2

Cl

2.75

—CH

2

CH

2

OCH

3

C

6

F

5

O—

2.76

—CH

2

CH═CH

2

2.77

C

6

F

5

O—

Example H5

Preparation of 1-(b-chloroethoxy)-3,5-diphenoxythiatriazine (process b

3

)

2.07 g (0.022 mol) of phenol are dissolved in 30 ml of tetrahydrofuran under nitrogen at a temperature of 40° C. to 45° C., and 0.90 g (0.0225 mol) of 60% sodium hydride is added. When no further hydrogen is evolved, the mixture is cooled to −40° C., 2.5 g (0.01 mol) of 1-(b-chloroethoxy)-3,5-dichlorothiatriazine are added in portions and the exothermic reaction is allowed to proceed at −30° C. to −40° C. The temperature is then allowed to rise to 0° C. and the reaction mixture is extracted with water and ethyl acetate. After removal of the solvent, 4.5 g of crude product are obtained, which, after purification by chromatography (silica gel; ethyl acetate/hexane 1/1) and recrystallization from 10 ml of ethyl acetate and 15 ml of hexane, gives 3.35 g (92% of theory) of the desired pure product of melting point 89-90° C.

Analysis: C

16

H

14

ClN

3

O

3

S;

calculated

found

[%]

[%]

N

11.55

11.69

Cl

9.74

9.73

Example H6

Preparation of 1-cyclohexyloxy-3-(p-nitrophenoxy)-5-(a-naphthoxy)thiatriazine (process c

3

)

0.65 g (0.0045 mol) of a-naphthol is dissolved in 40 ml of tetrahydrofuran, and 0.196 g (0.0045 mol) of 55% sodium hydride is added, under nitrogen. When the exothermic reaction has ended, the mixture is cooled to room temperature (23° C.) and a solution of 1.60 g (0.0043 mol) of 1-cyclohexyloxy-3-chloro-5-(p-nitrophenoxy)thiatriazine in a little tetrahydrofuran is added dropwise. During this operation, the temperature rises from 23° C. to 31° C. The mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed (silica gel; ethyl acetate/hexane 1/9). This gives 1.05 g of the desired pure product, which is recrystallized from 5 ml of ethyl acetate and 5 ml of hexane. The yield of crystalline product of melting point 115-116° C. is 0.87 g. The

13

C-NMR spectrum in CDCl

3

shows, in addition to the lines for the a-naphthyl radical (118-156 ppm), 4 lines for the cyclohexyl radical (79.3 ppm; 33.4 ppm; 24.9 ppm and 23.6 ppm) and 2 lines for the two C atoms of the thiatriazine ring (169.3 ppm and 168.2 ppm).

Example H7

Preparation of 1-(n-butoxy)-3,5-di(2′,5′-dichlorophenoxy)thiatriazine (process p)

0.75g (0.0015 mol) of 1-(b-chloroethoxy)-3,5-di(2′,5′-dichlorophenoxy)thiatriazine and 2.22 g (0.03 mol) of n-butanol are dissolved in 15 ml of tetrahydrofuran, the solution is cooled to −40° C. and 3.1 ml of a 0.098 molar solution of potassium tert-butylate in tetrahydrofuran (0.00030 mol) are added. After 45 minutes, the reaction has ended. The reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed (silica gel; ethyl acetate/hexane 8/92). The yield is 0.64 g (92% of theory) of a resin, the 300 MHz

1

H-NMR spectrum of which confirms the structure of the desired compound.

Example H8

Preparation of 1-(2,2-dimethylpropoxy)-3,5-di(pentafluorophenoxy)thiatriazine (process p)

0.74 g (0.001494 mol) of 1-methoxy-3,5-di(pentafluorophenoxy)thiatriazine is dissolved with 5.27 g (0.0598 mol) of 2,2-dimethyl-1-propanol in 15 ml of tetrahydrofuran, and 0.30 ml of a 0.0982 molar solution (2.94×10

−5

mol) of potassium tert-butylate in tetrahydrofuran is added at −60° C. After 30 minutes, the reaction has ended. The mixture is extracted with water and ethyl acetate, the extract is concentrated on a rotary evaporator and the residue is treated under a high vacuum at 50° C. The yield is 0.75 g (91% of theory) of a resin, the 300 MHz

1

H— and

13

C-NMR spectra of which are in agreement with the structure of the desired compound.

The compounds listed in the following Table 3 can be prepared analogously to Examples H5 to H8.

TABLE 3

Compounds of the formula V

(V)

Comp.

No.

Process

R

7

R

3

3.1

b

3

—CH

2

CH

2

Cl

3.2

—CH

2

CH

2

Cl

3.3

b

3

—CH

2

CH

2

Cl

C

6

F

5

O—

3.4

—CH

2

CH

2

Cl

3.5

b

3

3.6

b

3

C

6

F

5

O—

3.7

p

—(CH

2

)

3

CH

3

3.8

—CH

2

CH

2

Cl

3.9

—CH

2

CH

2

Cl

3.10

p

—CH

2

CH

2

C

6

H

5

3.11

—CH

2

CH

2

Cl

3.12

—CH

2

CH

2

Cl

3.13

b

3

—CH

2

CH

2

Cl

3.14

3.15

—CH

2

CH

2

Cl

3.16

—CH

2

CH

2

Cl

3.17

—CH

2

CH

2

Cl

3.18

C

6

F

5

O—

3.19

b

3

—CH

2

CH

2

Cl

3.20

—CH

2

CH

2

F

C

6

F

5

O—

3.21

—CH

2

CH

2

Cl

3.22

—CH

2

CH

2

Cl

3.23

b

3

—CH

2

CH

2

Cl

C

6

F

5

S—

3.24

c

3

3.25

—CH

2

CH

2

Cl

3.26

3.27

3.28

b

3

—CH

2

CH

2

Cl

3.29

—CH

2

CH

2

Cl

3.30

—CH

2

CH

2

Cl

3.31

c

3

3.32

3.33

—CH

2

C≡CH

3.34

—CH

2

CH

2

Cl

3.35

—CH

2

CH

2

Cl

3.36

p

3.37

—CH

2

CH

2

Cl

3.38

—CH

2

CH

2

Cl

3.39

3.40

p

C

6

F

5

S—

3.41

—CH

2

CH

2

Cl

3.42

—CH

2

CH

2

Cl

3.43

—CH

2

CH

2

Cl

3.44

—CH

2

CH

2

Cl

3.45

b

3

—CH

2

CH

2

Cl

3.46

C

6

F

5

O—

3.47

—CH

2

CH

2

Cl

3.48

p

3.49

—CH

2

CH

2

Cl

3.50

b

3

—CH

2

CH

2

Cl

3.51

—CH

2

CH

2

Cl

3.52

—CH

2

CH

2

Cl

3.53

3.54

—CH

2

CH

2

Cl

C

6

F

5

O—

3.55

—CH

2

CH

2

Cl

3.56

3.57

c

3

C

6

F

5

O—

3.58

—CH

2

CH

2

Cl

3.59

3.60

—CH

2

CH

2

Cl

3.61

p

—CH

3

3.62

3.63

—CH

2

CH

2

Cl

3.64

—CH

2

CH

2

Cl

3.65

—CH

2

CH

2

Cl

3.66

—CH

2

CH

2

Cl

3.67

b

3

C

6

F

5

O—

3.68

b

3

—CH

2

CH

2

Cl

3.69

—CH

2

CH

2

Cl

3.70

—CH

2

CH

2

Cl

3.71

3.72

p

—CH

3

C

6

F

5

O—

3.73

—CH

2

CH

2

Cl

3.74

—CH

2

CH

2

Cl

3.75

—CH

2

CH

2

Cl

3.76

3.77

b

3

—CH

2

CH

2

Cl

3.78

—CH

2

CH

2

Cl

3.79

—CH

2

CH

2

Cl

3.80

3.81

—CH

2

CH

2

Cl

3.82

b

3

—CH

2

CH

2

Cl

3.83

—CH

2

CH

2

Cl

3.84

p

—CH

2

C(CH

3

)

3

C

6

F

5

O—

3.85

—CH

2

CH

2

Cl

3.86

3.87

—CH

2

CH

2

Cl

3.88

—CH

2

CH

2

Cl

3.89

b

3

3.90

—CH

2

CH

2

Cl

3.91

—CH

2

CH

2

Cl

3.92

—CH

2

CH

2

Cl

3.93

b

3

—CH

2

CH

2

Cl

3.94

—CH

2

CH

2

Cl

3.95

—CH

2

CH

2

Cl

3.96

—CH

2

CH

2

Cl

3.97

b

3

3.98

—CH

2

CH

2

Cl

3.99

3.100

—CH

2

CH

2

Br

C

6

F

5

O—

3.101

—CH

2

CH

2

Cl

3.102

—CH

2

CH

2

Cl

3.103

p

—CH

3

3.104

—CH

2

CH

2

Cl

3.105

b

3

—CH

2

CH

2

Cl

3.106

—CH

2

CH

2

Cl

3.107

—CH

2

CH

2

Cl

3.108

—CH

2

CH

2

Cl

3.109

c

3

3.110

—CH

2

CH

2

Cl

3.111

—CH

2

CH

2

Cl

3.112

b

3

—CH

2

CH

2

Cl

3.113

—CH

2

CH

2

Cl

3.114

3.115

—CH

2

CH

2

Cl

3.116

—CH

2

CH

2

Cl

3.117

—CH

2

CH

2

Cl

3.118

—CH

2

CH

2

Cl

3.119

b

3

3.120

3.121

—CH

2

CH

2

Cl

3.122

—CH

2

CH

2

Cl

3.123

—CH

2

CH

2

Cl

3.124

p

—CH(CH

3

)(CH

2

)

5

CH

3

3.125

—CH

2

CH

2

Cl

3.126

—CH

2

CH

2

Cl

3.127

—CH

2

CH

2

Cl

3.128

—CH

2

CH

2

Cl

3.129

b

3

—CH

2

CH

2

Cl

3.130

b

3

—OC

6

F

5

3.131

b

3

—OC

6

F

5

3.132

—CH

2

CH

2

Cl

3.133

—CH

2

CH

2

Cl

3.134

—CH

2

CH

2

Cl

3.135

—CH

2

CH

2

Cl

3.136

b

3

—CH

2

CH

2

Cl

3.137

—CH

2

CH

2

Cl

3.138

—CH

2

CH

2

Cl

3.139

—CH

2

CH

2

Cl

3.140

b

3

—CH

2

CH

2

Cl

3.141

—CH

2

CH

2

Cl

3.142

b

3

—CH

2

CH

2

Cl

3.143

3.144

—CH

2

CH

2

Cl

3.145

—CH

2

CH

2

Cl

3.146

—CH

2

CH

2

Cl

C

6

F

5

O—

3.147

b

3

3.148

—CH

2

CH

2

Cl

3.149

—CH

2

CH

2

Cl

3.150

—CH

2

CH

2

Cl

3.151

—CH

2

CH

2

Cl

C

6

F

5

O—

3.152

—CH

2

CH

2

Cl

3.153

3.154

—CH

2

CH

2

Cl

3.155

b

3

—CH

2

CH

2

Cl

3.156

—CH

2

CH

2

Cl

3.157

3.158

—CH

2

CH

2

Cl

3.159

3.160

b

3

—CH

2

CH

2

Cl

3.161

—CH

2

CH

2

Cl

C

6

F

5

O—

3.162

—CH

2

CH

2

Cl

3.163

3.164

—CH

2

CH

2

Cl

3.165

—CH

2

CH

2

Cl

3.166

—CH

2

CH

2

Cl

3.167

—CH

2

CH

2

Cl

3.168

c

3

3.169

p

—CH

2

CH

2

CH

3

3.170

—CH

2

CH

2

Cl

3.171

—CH

2

CH

2

Cl

C

6

F

5

O—

3.172

—CH

2

CH

2

Cl

3.173

—CH

2

CH

2

Cl

3.174

3.175

—CH

2

CH

2

Cl

3.176

CH

2

CH

2

Cl

3.177

—CH

2

CH

2

Cl

3.178

—CH

2

CH

2

Cl

3.179

b

3

—CH

2

CH

2

Cl

3.180

—CH

2

CH

2

Cl

C

6

F

5

O—

3.181

—CH

2

CH

2

Cl

3.182

3.183

—CH

2

CH

2

Cl

3.184

3.185

—CH

2

CH

2

Cl

3.186

p

3.187

—CH

2

CH

2

Cl

3.188

—CH

2

CH

2

Cl

3.189

p

C

6

F

5

O—

3.190

—CH

2

CH

2

Cl

3.191

3.192

—CH

2

CH

2

Cl

3.193

—CH

2

CH

2

Cl

3.194

3.195

—CH

2

CH

2

Cl

3.196

b

3

—CH

2

CH

2

Cl

3.197

—CH

2

CH

2

Cl

3.198

3.199

—CH

2

CH

2

Cl

3.200

3.201

—CH

2

CH

2

Cl

3.202

p

—C

2

H

5

3.203

—CH

2

CH

2

Cl

3.204

—CH

2

CH

2

Cl

C

6

F

5

O—

3.205

—CH

2

CH

2

Cl

3.206

—CH

2

CH

2

Cl

3.207

p

—(CH

2

)

4

CH

3

3.208

—CH

2

CH

2

Cl

3.209

—CH

2

CH

2

Cl

3.210

3.211

—CH

2

CH

2

Cl

3.212

—CH

2

CH

2

Cl

3.213

—CH

2

CH

2

Cl

3.214

3.215

—CH

2

CH

2

Cl

3.216

—CH

2

CH

2

Cl

3.217

3.218

—CH

2

CH

2

Cl

3.219

p

3.220

—CH

2

CH

2

Cl

3.221

—CH

2

CH

2

Cl

3.222

—CH

2

CH

2

Cl

3.223

C

6

F

5

O—

3.224

C

6

F

5

O—

3.225

3.226

3.227

C

6

F

5

O—

3.228

C

6

F

5

O—

3.229

3.230

C

6

F

5

O—

3.231

3.232

p

—OC

6

F

5

3.233

p

—CH

2

CH

2

Si(CH

3

)

3

—OC

6

F

5

3.234

p

—OC

6

F

5

3.235

p

—(CH

2

)

3

Si(CH

3

)

3

—OC

6

F

5

3.236

p

—OC

6

F

5

3.237

p

—OC

6

F

5

3.238

p

—CH

2

C

6

F

5

—OC

6

F

5

3.239

p

—OC

6

F

5

3.240

p

—OC

6

F

5

3.241

p

—CH

2

Si(CH

3

)

3

—OC

6

F

5

3.242

p

—OC

6

F

5

3.243

p

—OC

6

F

5

3.244

p

—OC

6

F

5

3.245

p

—CH(CH

3

)C

6

F

5

—OC

6

F

5

3.246

p

—OC

6

F

5

3.247

p

—OC

6

F

5

3.248

p

—CH(CH

3

)Si(CH

3

)

3

—OC

6

F

5

3.249

p

—OC

6

F

5

3.250

—CH(CH

3

)COOCH

3

—OC

6

F

5

3.251

b

3

—CH

2

CH

2

Cl

3.252

p

—C

2

H

5

—SC

6

F

5

3.253

p

—CH

3

—SC

6

F

5

3.254

p

—CH(CH

3

)

2

—SC

6

F

5

3.255

p

—CH

2

CH

2

Si(CH

3

)

3

—OCH

2

CH

2

Cl

3.256

p

—CH

2

CH

2

CH

2

Si(CH

3

)

3

—OCH

2

CH

2

Cl

3.257

p

Adamantyl

—OCH

2

CH

2

Cl

3.258

p

—CH

2

Si(CH

3

)

3

—OCH

2

CH

2

Cl

3.259

p

—OC

6

F

5

3.260

p

—CH(CH

3

)Si(CH

3

)

3

—OC

6

F

5

3.261

p

3.262

p

3.263

p

3.264

p

—CH

2

Si(CH

3

)

3

3.265

p

3.266

3.267

p

3.268

p

3.269

p

3.270

p

—OC

6

F

5

3.271

—OC

6

F

5

3.272

—OC

6

F

5

3.273

p

—OC

6

F

5

3.274

p

—OC

6

F

5

3.275

p

—OC

6

F

5

3.276

p

—OC

6

F

5

3.277

p

—OC

6

F

5

3.278

p

—OC

6

F

5

3.279

p

—OC

6

F

5

3.280

—OC

6

F

5

3.281

p

—OC

6

F

5

3.282

—OC

6

F

5

3.283

—OC

6

F

5

3.284

p

—OC

6

F

5

3.285

p

—OC

6

F

5

3.286

p

—OC

6

F

5

3.287

p

—OC

6

F

5

3.288

p

—OC

6

F

5

3.289

—OC

6

F

5

3.290

—OC

6

F

5

3.291

—OC

6

F

5

3.292

p

—OC

6

F

5

3.293

—OC

6

F

5

3.294

—OC

6

F

5

3.295

p

—OC

6

F

5

3.296

p

—OC

6

F

5

3.297

—OC

6

F

5

3.298

—OC

6

F

5

3.299

p

—OC

6

F

5

3.300

—OC

6

F

5

3.301

—OC

6

F

5

3.302

—OC

6

F

5

3.303

—OC

6

F

5

3.304

—OC

6

F

5

3.305

—OC

6

F

5

3.306

—OC

6

F

5

3.307

—OC

6

F

5

3.308

—OC

6

F

5

Comp. No.

R

12

—X

1

3.1

3.2

3.3

C

6

F

5

O—

3.4

C

6

F

5

S—

3.5

3.6

C

6

F

5

O—

3.7

3.8

3.9

3.10

3.11

3.12

C

6

F

5

S—

3.13

3.14

3.15

C

6

F

5

S—

3.16

3.17

C

6

Cl

5

O—

3.18

C

6

F

5

O—

3.19

3.20

C

6

F

5

O—

3.21

3.22

3.23

C

6

F

5

S—

3.24

3.25

3.26

3.27

3.28

3.29

3.30

3.31

3.32

3.33

3.34

3.35

3.36

3.37

3.38

3.39

3.40

C

6

F

5

S—

3.41

3.42

3.43

3.44

3.45

3.46

C

6

F

5

O—

3.47

3.48

3.49

3.50

3.51

3.52

3.53

3.54

3.55

3.56

3.57

3.58

3.59

3.60

3.61

3.62

3.63

3.64

3.65

3.66

3.67

C

6

F

5

O—

3.68

3.69

3.70

3.71

3.72

C

6

F

5

O—

3.73

3.74

3.75

3.76

3.77

3.78

3.79

3.80

3.81

3.82

3.83

3.84

C

6

F

5

O—

3.85

3.86

3.87

3.88

3.89

3.90

3.91

3.92

3.93

3.94

3.95

3.96

3.97

3.98

3.99

3.100

C

6

F

5

O—

3.101

3.102

3.103

3.104

3.105

3.106

3.107

3.108

3.109

—SC

6

F

5

3.110

3.111

3.112

3.113

3.114

3.115

3.116

3.117

3.118

3.119

3.120

3.121

3.122

3.123

3.124

3.125

3.126

3.127

3.128

3.129

3.130

—OC

6

F

5

3.131

—OC

6

F

5

3.132

3.133

3.134

3.135

3.136

3.137

3.138

3.139

3.140

3.141

3.142

3.143

3.144

3.145

3.146

3.147

3.148

3.149

C

6

F

5

S—

3.150

C

6

F

5

O—

3.151

3.152

3.153

3.154

3.155

3.156

3.157

3.158

3.159

3.160

3.161

3.162

3.163

3.164

C

6

F

5

O—

3.165

3.166

3.167

3.168

—C

6

F

5

S—

3.169

3.170

C

6

F

5

O—

3.171

C

6

F

5

S—

3.172

3.173

3.174

3.175

3.176

3.177

3.178

3.179

3.180

3.181

3.182

3.183

3.184

3.185

3.186

3.187

3.188

3.189

C

6

F

5

O—

3.190

3.191

3.192

3.193

3.194

3.195

3.196

3.197

3.198

3.199

3.200

3.201

3.202

3.203

3.204

3.205

3.206

3.207

3.208

3.209

3.210

3.211

3.212

3.213

C

6

F

5

O—

3.214

3.215

3.216

3.217

3.218

3.219

3.220

3.221

3.222

3.223

C

6

F

5

O—

3.224

C

6

F

5

O—

3.225

3.226

3.227

C

6

F

5

O—

3.228

C

6

F

5

O—

3.229

3.230

C

6

F

5

O—

3.231

3.232

—OC

6

F

5

3.233

—OC

6

F

5

3.234

—OC

6

F

5

3.235

—OC

6

F

5

3.236

—OC

6

F

5

3.237

—OC

6

F

5

3.238

—OC

6

F

5

3.239

—OC

6

F

5

3.240

—OC

6

F

5

3.241

—OC

6

F

5

3.242

—OC

6

F

5

3.243

—OC

6

F

5

3.244

—OC

6

F

5

3.245

—OC

6

F

5

3.246

—OC

6

F

5

3.247

—OC

6

F

5

3.248

—OC

6

F

5

3.249

—OC

6

F

5

3.250

—OC

6

F

5

3.251

3.252

—SC

6

F

5

3.253

—SC

6

F

5

3.254

—SC

6

F

5

3.255

—OC

6

F

5

3.256

—OC

6

F

5

3.257

—OC

6

F

5

3.258

—OC

6

F

5

3.259

—OC

6

F

5

3.260

—OC

6

F

5

3.261

3.262

3.263

3.264

3.265

3.266

3.267

3.268

3.269

3.270

—OC

6

F

5

3.271

—OC

6

F

5

3.272

—OC

6

F

5

3.273

—OC

6

F

5

3.274

—OC

6

F

5

3.275

—OC

6

F

5

3.276

—OC

6

F

5

3.277

—OC

6

F

5

3.278

—OC

6

F

5

3.279

—OC

6

F

5

3.280

—OC

6

F

5

3.281

—OC

6

F

5

3.282

—OC

6

F

5

3.283

—OC

6

F

5

3.284

—OC

6

F

5

3.285

—OC

6

F

5

3.286

—OC

6

F

5

3.287

—OC

6

F

5

3.288

—OC

6

F

5

3.289

—OC

6

F

5

3.290

—OC

6

F

5

3.291

—OC

6

F

5

3.292

—OC

6

F

5

3.293

—OC

6

F

5

3.294

—OC

6

F

5

3.295

—OC

6

F

5

3.296

—OC

6

F

5

3.297

—OC

6

F

5

3.298

—OC

6

F

5

3.299

—OC

6

F

5

3.300

—OC

6

F

5

3.301

—OC

6

F

5

3.302

—OC

6

F

5

3.303

—OC

6

F

5

3.304

—OC

6

F

5

3.305

—OC

6

F

5

3.306

—OC

6

F

5

3.307

—OC

6

F

5

3.308

—OC

6

F

5

Physical data of compounds in Table 3:

Comp. No.

Physical Data

3.1

Melting point 89-90° C.

3.3

Melting point 82-83° C.

3.5

1

H-NMR: 6.9-7.3 ppm (8H); 4.3 ppm (1H);

3.95 ppm (1H); 3.8 ppm (6H); 1.2-2.2 ppm (12H)

3.6

Melting point 104-105° C.

3.7

1

H-NMR: 7.3 ppm (2H); 7.1 ppm (4H);

3.8 ppm (2H); 1.6 ppm (2H); 1.4 ppm (2H);

0.9 ppm (3H)

3.10

1

H-NMR: 6.8-7.4 ppm (6H); 3.9 ppm (2H);

3.0 ppm (2H)

3.13

Melting point 184-186° C.

3.19

1

H-NMR: 7.1-8.0 ppm (8H); 4.1 ppm (2H);

3.6 ppm (2H); 3.35 ppm (3H)

3.23

Melting point 89-90° C.

3.24

1

H-NMR: 7.6 ppm (2H); 7.4 ppm (1H);

6.9 ppm (1H); 5.5 ppm (1H); 4.4 ppm (1H);

1.4-1.9 ppm (14H)

3.28

1

H-NMR: 10.05 ppm (2H); 7.1-7.9 ppm (8H);

4.1 ppm (2H); 3.65 ppm (2H)

3.31

Melting point 115-116° C.

3.36

1

H-NMR: 7.6-7.7 ppm (2H); 7.1-7.3 ppm (4H);

5.3-5.5 ppm (1H); 4.3-4.5 ppm (1H)

3.40

13

C-NMR: 173.8 ppm; 135-150 ppm; 79.0 ppm

22.0-47.4 ppm (7 signals)

3.45

Melting point 83-84° C.

3.48

1

H-NMR: 6.5-7.4 ppm (11H); 5.7 ppm (1H);

1.6 ppm (3H)

3.50

1

H-NMR: 7.05 ppm (2H); 6.85 ppm (2H);

4.7 ppm (2H); 4.2 ppm (4H); 4.0 ppm (2H)

3.6 ppm (2H); 1.6 ppm (6H); 1.3 ppm (6H)

3.57

1

H-NMR: 7.1-7.9 ppm (12H); 4.95 ppm (1H);

4.1 ppm (2H)

3.61

Melting point 100-102° C.

3.67

13

C-NMR: 167.9 ppm; 136-143 ppm; 86.7 ppm;

62.5 ppm; 33.4 ppm; 30.6 ppm; 21.0 ppm

3.68

Melting point 141-142° C.

3.72

Melting point 86-87° C.

3.77

1

H-NMR: 8.85 ppm (2H); 7.4 ppm (2H);

7.15 ppm (2H); 4.05 ppm (2H); 3.6 ppm (2H);

2.6 ppm (6H)

3.82

1

H-NMR: 7.9 ppm (2H); 7.6 ppm (2H);

7.4 ppm (4H); 4.0 ppm (2H); 3.9 ppm (6H);

3.6 ppm (2H)

3.84

13

C-NMR: 168.2 ppm; 136-143 ppm; 73.8 ppm;

31.6 ppm; 25.9 ppm

3.89

Melting point 126-127° C.

3.93

Melting point 173-174° C.

3.97

Melting point 108-109° C.

3.103

Melting point 100-102° C.

3.105

Melting point 169-170° C.

3.109

13

C-NMR: 177.9 ppm; 162.9 ppm; 103.2 ppm;

83.5 ppm

3.112

1

H-NMR: 8.6 ppm (2H); 7.7 ppm (4H);

7.3 ppm (2H); 4.0 ppm (2H); 3.6 ppm (2H)

3.119

Melting point 80-81° C.

3.124

1

H-NMR: 7.1-7.3 ppm (6H); 4.35 ppm (1H);

1.6 ppm (2H); 1.3 ppm (11H); 0.9 ppm (3H)

3.129

1

H-NMR: 6.4 ppm (2H); 6.3 ppm (4H);

4.0 ppm (2H); 3.8 ppm (12H); 3.6 ppm (2H)

3.130

13

C-NMR: 167.4 ppm; 147.7 ppm; 109.7 ppm;

88.2 ppm; 62.2 ppm; 36.5 ppm; 34.0 ppm;

32.0 ppm; 26.3 ppm; 25.4 ppm; 20.6 ppm

3.131

13

C-NMR: 167.4 ppm; 147.8 ppm; 109.5 ppm;

83.1 ppm; 68.1 ppm; 37.1 ppm; 35.7 ppm; 33.0 ppm;

29.5 ppm; 26.2 ppm; 20.5 ppm

3.136

Melting point 96-97° C.

3.140

Melting point 86-87° C.

3.142

1

H-NMR: 7.3 ppm (2H); 7.15 ppm (4H);

4.0 ppm (2H); 3.6 ppm (2H)

3.147

1

H-NMR: 7.2 ppm (2H); 6.6 ppm (2H);

6.4 ppm (2+2H); 4.4 ppm (1H); 3.7 ppm (2H);

3.5 ppm (2H); 2.9 ppm (12H)

3.155

Melting point 101-102° C.

3.160

1

H-NMR: 7.1 ppm (2H); 6.9 ppm (4H);

4.0 ppm (2H); 3.6 ppm (2H)

3.168

13

C-NMR: 177.9 ppm; 162.9 ppm; 103.2 ppm;

83.5 ppm

3.169

Melting point 197-198° C.

3.179

Melting point 100-101° C.

3.186

1

H-NMR: 6.8-7.4 ppm (6H); 4.7 ppm (2H)

3.189

13

C-NMR: 167.8 ppm; 136.2-143.1 ppm; 83.2 ppm;

34.0 ppm; 23.2 ppm

3.196

Melting point 106-108° C.

3.202

Melting point 89-90° C.

3.207

1

H-NMR: 6.9-7.2 ppm (6H); 3.7 ppm (2H)

1.7 ppm (2H); 1.3 ppm (4H); 0.9 ppm (3H)

3.219

1

H-NMR: 6.8-7.1 ppm (6H); 4.15 ppm (1H)

1.2-1.9 ppm (10H)

3.224

Melting point 85-86° C.

3.232

13

C-NMR: 168.2 ppm; 142.4 ppm; 120.3 ppm;

63.3 ppm; 45.6 ppm; 40.6 ppm; 38.0 ppm; 36.3 ppm;

31.5 ppm; 31.3 ppm; 26.1 ppm; 21.0 ppm

3.233

13

C-NMR: 168.1 ppm; 136-143 ppm; 64.2 ppm;

18.2 ppm; −1.9 ppm

3.234

Melting point 126-127° C.

3.235

13

C-NMR: 168.1 ppm; 136-143 ppm; 68.0 ppm;

24.0 ppm; 12.3 ppm; −1.99 ppm

3.236

Melting point 99-100° C.

3.237

13

C-NMR: 171.4 ppm; 168.2 ppm; 137.6 ppm;

136.2-142.8 ppm; 62.0 ppm; 36.8 ppm; 8.6 ppm

3.239

Melting point 113-114° C.

3.240

Melting point 93-94° C.

3.241

13

C-NMR: 168.53 ppm; 54.59 ppm; −3.54 ppm;

3.243

13

C-NMR: 167.9 ppm; 167.6 ppm; 119.1 ppm;

84.1 ppm; 44.2 ppm; 33.6 ppm; 28.4 ppm; 24.9 ppm;

21.7 ppm; 15.8 ppm

3.244

13

C-NMR: 168.0 ppm; 167.7 ppm; 119.0 ppm;

85.8 ppm; 45.7 ppm; 32.6 ppm; 28.7 ppm; 28.5 ppm;

22.1 ppm; 21.7 ppm; 15.8 ppm

3.246

13

C-NMR: 167.7 ppm; 81.2 ppm; 33.6 ppm;

33.0 ppm; 31.2 ppm; 21.5 ppm

3.247

13

C-NMR: 167.7 ppm; 78.2 ppm; 31.3 ppm;

30.9 ppm; 28.6 ppm; 21.7 ppm

3.248

Melting point 48-49° C.

3.249

1

H-NMR: 5.8 ppm (1H); 5.0 ppm (2H);

4.2 ppm (1H); 0 ppm (9H)

3.251

Melting point 185-186° C.

3.252

13

C-NMR: 174.5 ppm; 62.5 ppm; 15.0 ppm;

3.253

Melting point 90-92° C.

3.254

13

C-NMR: 173.8 ppm; 75.7 ppm; 23.6 ppm;

3.255

1

H-NMR: 4.55 ppm (2H); 3.2 ppm (4H);

1.0 ppm (2H); 0 ppm (9H)

3.256

1

H-NMR: 4.6 ppm (2H); 3.75 ppm (2H);

3.6 ppm (2H); 1.6 ppm (2H); 0.5 ppm (2H);

0 ppm (9H)

3.257

1

H-NMR: 4.6 ppm (2H); 3.8 ppm (2H);

3.2 ppm (2H); 2.0 ppm (3H); 1.4-1.8 ppm (6H)

3.258

1

H-NMR: 4.5 ppm (2H); 3.7 ppm (2H);

3.0 ppm (2H); 0 ppm (9H)

3.259

13

C-NMR: 167.7 ppm; 78.2 ppm; 31.3 ppm;

30.9 ppm; 28.6 ppm; 21.7 ppm

3.260

Melting point 48-49° C.

3.261

Melting point 95-96° C.

3.262

Melting point 131-132° C.

3.263

1

H-NMR: 7.0 ppm (2H); 4.55 ppm (1H);

0.8-2.0 ppm (16H)

3.264

Melting point 83-84° C.

3.265

Melting point 103-104° C.

3.267

13

C-NMR: 167.7 ppm; 138.9-147.6 ppm;

103.1-103.7 ppm; 51.0 ppm; 46.3 ppm; 34.7 ppm;

32.9 ppm; 27.5 ppm

3.268

Melting point 74-75° C.

3.269

Melting point 112-113° C.

3.270

13

C-NMR: 167.7 ppm; 136-143 ppm; 81.9 ppm;

35.0 ppm; 34.4 ppm; 33.9 ppm; 31.2 ppm; 28.9 ppm;

26.1 ppm; 21.1 ppm

3.273

13

C-NMR: 168.0 ppm; 167.8 ppm; 139.0 ppm;

130.7 ppm; 125-143.0 ppm; 79.6 ppm; 47.6 ppm;

47.5 ppm; 42.2 ppm; 35.1 ppm

3.274

13

C-NMR: 168.0 ppm; 187.8 ppm; 142.3 ppm;

131.6 ppm; 80.4 ppm; 49.0 ppm; 46.0 ppm; 40.7 ppm;

35.3 ppm

3.275

13

C-NMR: 167.8 ppm; 125-143 ppm; 75.9 ppm;

36.3 ppm (q); 30.8 ppm; 30.7 ppm; 29.6 ppm;

23.7 ppm; 18.4 ppm

3.276

13

C-NMR: 168.1 ppm; 138.3 ppm; 131.4 ppm;

125-143 ppm; 68.4 ppm; 49.4 ppm; 43.7 ppm;

42.3 ppm; 38.2 ppm; 29.1 ppm

3.277

13

C-NMR: 167.8 ppm; 125-143 ppm; 80.7 ppm;

42.0 ppm; 37.4 ppm; 37.3 ppm; 36.4 ppm; 29.0 ppm;

20.6 ppm

3.278

13

C-NMR: 167.8 ppm; 125-143 ppm; 83.1 ppm;

43.3 ppm; 40.3 ppm; 35.4 ppm; 34.9 ppm;

27.8 ppm; 24.1 ppm

3.279

13

C-NMR: 167.7 ppm; 127-143 ppm; 73.5 ppm;

45.5 ppm (q); 31.8 ppm; 23.9 ppm; 19.8 ppm;

19.5 ppm

3.281

13

C-NMR: 167.9 ppm; 167.4 ppm; 125-143 ppm;

81.8 ppm; 47.5 ppm; 44.8 ppm; 41.4 ppm; 38.4 ppm;

36.8 ppm; 33.9 ppm; 27.2 ppm; 23.7 ppm; 19.4 ppm

3.284

Melting point 123-124° C.

3.285

Melting point 117-118° C.

3.286

Melting point 109-110° C.

3.287

13

C-NMR: 167.9 ppm; 167.7 ppm; 136-143 ppm;

119.1 ppm; 83.0 ppm; 41.6 ppm; 33.4 ppm;

28.8 ppm; 21.8 ppm; 17.2 ppm

3.288

13

C-NMR: 167.9 ppm; 167.7 ppm; 136-143 ppm;

117.4 ppm; 84.3 ppm; 42.8 ppm; 32.5 ppm;

28.6 ppm; 21.9 ppm; 19.8 ppm

3.292

Melting point 82-83° C.

3.295

13

C-NMR: 167.5 ppm; 157.7 ppm; 136-143 ppm;

131.5 ppm; 128.6 ppm; 124.3 ppm; 120.5 ppm;

110.3 ppm; 78.6 ppm; 55.1 ppm; 38.8 ppm;

30.4 ppm; 21.4 ppm

3.296

13

C-NMR: 168.3 ppm; 126-143 ppm; 136.3 ppm;

135.2 ppm; 133.4 ppm; 129.6 ppm; 128.9 ppm;

127.5 ppm; 67.0 ppm; 39.9 ppm; 33.3 ppm;

20.0 ppm; 13.8 ppm

3.299

13

C-NMR: 168.4 ppm; 126-143 ppm; 65.9 ppm;

Example H9

Preparation of 1,3,5-trimethoxythiatriazine (process a

3

)

2.04 g (0.02 mol) of trichlorothiatriazine are dissolved in 15 ml of tetrahydrofuran and a solution of 5.94 g (0.033 mol) of 30% methanolic sodium methylate solution in 20 ml of tetrahydrofuran is added dropwise at 30° C., while cooling. After 15 minutes, the reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed over silica gel with ethyl acetate/hexane 1/3 as the eluting agent. The yield of the desired product is 1.70 g (89% of theory).

Analysis: C

5

H

9

N

3

O

3

S;

calculated [%]

found [%]

N

21.98

21.98

S

16.77

16.25

Example H10

Preparation of 1,3-dimethoxy-5-(2′,5′-difluorophenoxy)thiatriazine (process d

3

)

3.05 g (0.007 mol) of 1-(β-chloroethoxy)-3,5-di(2′,5′-difluorophenoxy)thiatriazine are dissolved in 20 ml of methanol. 10.4 ml of a 1.35 molar sodium methylate solution in methanol are slowly added dropwise at −60° C., the intermediate 1-methoxy-3,5-di(2′,5′-difluorophenoxy)thiatriazine crystallizing out. The mixture is warmed gradually to +5° C., the intermediate reacting further to give the desired end product. The reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed over silica gel. The yield of desired product is 1.38 g (68% of theory). After recrystallization from a mixture of cyclohexane/toluene 6/1, the product melts at 75-76° C.

Analysis: C

10

H

9

N

3

O

3

F

2

S;

calculated

found

[%]

[%]

C

41.52

41.68

H

3.14

3.19

N

14.53

14.44

0.30 g of 1,3,5-trimethoxythiatriazine (Example H9) is isolated as a by-product.

Example H11

Preparation of 1-(β-chloroethoxy)-3,5-di(trichloroethoxy)thiatriazine (process d

3

)

1.80 g (0.0036 mol) of 1-(β-chloroethoxy)-3,5-di(2′,4′-dichlorophenoxy)thiatriazine are dissolved in 20 ml of tetrahydrofuran and the solution is cooled to −50° C. A solution prepared from 1.12 g (0.0075 mol) of trichloroethanol and 0.33 g of 55% sodium hydride (0.0075 mol) is added dropwise to this solution. The reaction is exothermic. The reaction mixture is warmed to 0° C., extracted with water and ethyl acetate, and the product is chromatographed over silica gel. The yield is 1.62 g (95% of theory). The desired compound is a resin, the

1

H— and

13

C-NMR spectra of which confirm the structure.

Example H12

Preparation of 1-(β-chloroethoxy)-3,5-di-tert-butylmercaptothiatriazine and 1-(β-chloroethoxy)-3-chloro-5-tert-butylmercaptothiatriazine (process b

1

)

3.00 g (0.012 mol) of 1-(β-chloroethoxy)-3,5-dichlorothiatriazine are dissolved in 20 ml of tetrahydrofuran, and a solution of 3.25 g (0.036 mol, of tert-butylmercaptan and 3.64 g (0.036 mol) of trethylamine in 15 ml of tetrahydrofuran is added dropwise at −50° C. Thereafter, the mixture warmed to 0° C., extracted with water and ethyl acetate, and the substance mixture is separated over silica gel with ethyl acetate/hexane 3/1 as the eluting agent. 1.05 g of 1-(β-chloroethoxy)-3-chloro-5-tert-butylmercaptothiatriazine and 0.25 g of 1-(β-chloroethoxy)-3,5-di-tert-butylmercaptothiatriazine are obtained as resins. The

1

H-NMR spectra and the mass spectra confirm the structures.

The compounds listed in the following Table 4 can be prepared analogously to Examples H9 to H12.

TABLE 4

Compounds of the formula IV

(IV)

Comp.

Proc-

No.

ess

R

7

R

3

R

2

4.1

c

2

—CH

3

—OCH

3

4.2

a

3

—CH

3

—OCH

3

—OCH

3

4.3

—OCH

3

4.4

b

1

—CH

2

CH

2

Cl

Cl

—SCH(CH

3

)

2

4.5

d

3

—CH

3

—OCH

3

4.6

—C

2

H

5

—OC

2

H

5

4.7

—CH

3

—OCH

3

4.8

d

3

—CH

2

CH

2

Cl

—OC

2

H

5

—OC

2

H

5

4.9

d

3

—CH

3

—OCH

3

4.10

—SCH

3

4.11

—CH

2

CH═CH

2

—OCH

2

CH═CH

2

4.12

d

3

—CH

3

—OCH

2

C≡CH

4.13

—CH

2

CH

2

Cl

—SCH

3

4.14

—CH

2

CH

2

Cl

—SCH

3

4.15

a

3

—Ch

2

CH

2

CH

3

Cl

—OCH

2

CH

2

CH

3

4.16

d

3

—CH

3

C

6

F

5

O—

—OCH

3

4.17

—CH

3

—OCH

3

4.18

b

1

—CH

2

CH

2

Cl

—SCH(CH

3

)

2

—SCH(CH

3

)

2

4.19

4.20

d

3

—C

2

H

5

—OC

2

H

5

4.21

—OCH

3

4.22

b

1

—CH

2

CH

2

Cl

Cl

—SC(CH

3

)

3

4.23

d

3

—CH

2

CH

2

Cl

—OCH

2

CF

3

—OCH

2

CF

3

4.24

—CH

3

—OCH

3

4.25

—SC

2

H

5

4.26

a

3

—CH

2

CH

2

CH

3

—OCH

2

CH

2

CH

3

—OCH

2

CH

2

CH

3

4.27

—CH

3

—OCH

3

4.28

—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.29

d

3

—CH

2

CH

2

Cl

—OCH

2

CBr

3

—OCH

2

CBr

3

4.30

—CH

2

CH

2

Cl

—SCH

3

4.31

—CH

3

4.32

—C

4

H

9

(n)

—OC

4

H

9

(n)

4.33

d

3

—C

2

H

5

—OCH

3

—OCH

3

4.34

—C

2

H

5

—OC

2

H

5

4.35

—CH

3

—OC

6

F

5

4.36

—CH

2

CH

2

Cl

—OC(CH

3

)

3

4.37

—CH

3

—OCH

3

4.38

d

3

—CH

2

CH

2

Cl

—OCH

2

CCl

3

—OCH

2

CCl

3

4.39

—SCH

3

—SCH

3

4.40

—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.41

d

3

—C

2

H

5

—OC

2

H

5

4.42

—CH

3

—OCH

3

4.43

d

3

—CH

3

—OCH

3

4.44

—CH

3

—OCH

3

4.45

d

3

C

6

F

5

O—

—CH

2

CH

2

Cl

4.46

—SC

2

H

5

—SC

2

H

5

4.47

—CH

3

—OCH

3

4.48

—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.49

b

1

—CH

2

CH

2

Cl

—SC(CH

3

)

3

—SC(CH

3

)

3

4.50

d

3

—C

2

H

5

—OC

2

H

5

—OC

2

H

5

4.51

—OCH

3

—OCH

3

4.52

—CH

2

CH

2

Cl

C

6

F

5

O—

—SCH

3

4.53

—CH

2

CH

2

Cl

—OCH

3

4.54

—CH

2

CH

2

Cl

—SCH(CH

3

)

2

4.55

—CH(CH

3

)

2

—OCH(CH

3

)

2

4.56

—SCH

3

—SCH

3

4.57

—CH

3

—OCH

3

4.58

—OC

2

H

5

4.59

—CH

2

CH

2

Cl

—SCH

3

4.60

—CH

2

C≡CH

C

6

F

5

O—

—OCH

3

4.61

—CH

2

C≡CH

—OCH

3

4.62

C

6

F

5

O—

—SCH

3

4.63

—C

2

H

5

—OC

2

H

5

4.64

—CH

2

CH

2

Cl

—SCH

3

4.65

—CH

3

—OCH

3

4.66

—CH

3

—OCH

3

4.67

—S—CH(CH

3

)

2

—S—CH(CH

3

)

2

4.68

—CH

3

—OCH

3

4.69

C

6

F

5

O—

—OCH

3

4.70

—CH

2

CH

2

Cl

—SCH

3

4.71

—CH

2

CH

2

Cl

—OCH(CH

3

)C

2

H

5

4.72

—SC(CH

3

)

2

—SC(CH

3

)

3

4.73

—CH

3

—OCH

3

4.74

—CH

3

—OCH

3

4.75

—C

2

H

5

—OC

2

H

5

4.76

—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.77

—CH

3

—SCH

3

4.78

—CH

3

—OCH

3

4.79

—C

3

H

7

(n)

—OC

3

H

7

(n)

4.80

—SCH

3

—SCH

3

4.81

—CH

3

—OCH

3

4.82

—CH

3

—OCH

3

4.83

—SC

2

H

5

—SC

2

H

5

4.84

—CH

2

CH

2

Cl

—SCH

3

4.85

—CH

2

CH

2

Cl

4.86

d

3

—CH

3

—OCH

3

4.87

—SC

4

H

9

(n)

4.88

—CH

3

—OCH

3

4.89

4.90

—CH(CH

3

)C

2

H

5

—OCH(CH

3

)C

2

H

5

4.91

C

6

F

5

O—

—OCH

3

4.92

—CH

3

—OCH

3

4.93

—CH

2

CH═CH

2

—SCH

3

—SCH

3

4.94

—CH

2

CH═CH

2

—OCH

3

4.95

C

6

F

5

O—

—OCH

3

4.96

—CH

2

CH

2

Cl

—OCH

3

4.97

—CH

2

CH

2

Cl

—SCH

3

4.98

—C

2

H

5

—OC

2

H

5

4.99

—CH

3

—OCH

3

4.100

—CH

3

—SCH

3

4.101

—SC

2

H

5

4.102

—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.103

—CH

3

—OCH

3

4.104

4.105

—CH

2

CH

2

OCH

3

—SCH

4

H

9

(i)

4.106

—OCH

3

—OCH

3

4.107

4.108

—C

2

H

5

—OC

2

H

5

4.109

—CH

3

4.110

—CH

2

CH

2

Cl

C

6

F

5

O—

4.111

—C

2

H

5

—OC

2

H

5

4.112

—SCH

3

—SCH

3

4.113

—SC

2

H

5

4.114

C

6

F

5

O—

—OCH

3

4.115

C

6

F

5

O—

—SCH

3

4.116

—CH

3

C

6

F

5

O—

4.117

—SCH

3

—SCH

3

4.118

—CH

3

C

6

F

5

O—

4.119

—CH

2

C≡CH

C

6

F

5

O—

4.120

—CH

2

CH

2

F

—OCH

2

CH

2

F

4.121

—C

7

H

15

(n)

—SCH

3

—SCH

3

4.122

—C

5

H

11

(n)

—OC

5

H

11

(n)

4.123

—S—CH(CH

3

)

2

—S—CH(CH

3

)

2

4.124

—SC

2

H

5

—SC

2

H

5

4.125

—SCH

3

—SCH

3

4.126

—S—CH(CH

3

)

2

—S—CH(CH

3

)

2

4.127

—CH

2

CH

2

Cl

4.128

—CH

3

—OCH

2

CH

2

SC

2

H

5

4.129

—SCH

3

4.130

—O—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.131

—SCH

3

—SCH

3

4.132

—CH(CH

3

)

2

—O—CH(CH

3

)

2

4.133

—C

2

H

5

—OC

2

H

5

4.134

—SCH

3

—SCH

3

4.135

—OCH

2

CF

3

—OCH

2

CF

3

4.136

—CH

3

—OCH

3

4.137

Cl

—OCH

3

4.138

Cl

—S—CH(CH

3

)

2

4.139

—CH

3

—OCH

3

Cl

4.140

—CH

2

C≡CH

Cl

4.141

—CH

2

C≡CH

Cl

—SC

3

H

7

(n)

4.142

—CH

3

Cl

—SC(CH

3

)

3

4.143

Cl

—OC

3

H

7

(n)

4.144

—CH

2

CH

2

F

Cl

4.145

Cl

—OCH

3

4.146

Cl

—SC

2

H

5

4.147

—SCH

2

CH(CH

3

)C

2

H

5

Cl

4.148

—CH

2

CH

2

Br

Cl

—SCH

2

CH═CH

2

4.149

—C

2

H

5

Cl

—OC

2

H

5

4.150

—CH

2

C≡CH

—SCH

2

CF

3

Cl

4.151

—C

4

H

9

(n)

Cl

—OC

4

H

9

(n)

4.152

—C

4

H

9

(n)

Cl

—SC

4

H

9

(n)

4.153

—OC

2

H

5

—OC

2

H

5

4.154

—CH(CH

3

)

2

—SCH

2

CF

3

—SCH

2

CF

3

4.155

Cl

4.156

d

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.157

d

3

—CH

2

CH

2

Si(CH

3

)

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.158

d

3

—(CH

2

)

3

Si(CH

3

)

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.159

d

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.160

d

3

—CH

2

Si(CH

3

)

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.161

d

3

—CH

3

—OCH

3

4.162

d

3

—C

2

H

5

—OC

2

H

5

4.163

d

3

—CH

3

—OCH

3

4.164

d

3

—C

2

H

5

—SC

6

F

5

—OC

2

H

5

4.165

d

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.166

d

3

—OCH

2

CH

2

Cl

4.167

d

3

—OC

6

F

5

—OCH

2

CH

2

Cl

4.168

d

3

—OCH

2

CH

2

Cl

—OC

6

F

5

—OCH

2

CH

2

Cl

4.169

d

3

—OC

6

F

5

—OCH

2

CH

2

Cl

Physical data of compounds in Table 4:

Comp. No.

Physical data

4.1

1

H-NMR: 7.4 ppm (2H); 7.25 ppm (1H); 7.15 ppm (2H);

3.9 ppm (3H); 3.5 ppm (3H)

4.2

13

C-NMR: 169.5 ppm; 54.7 ppm; 49.1 ppm

4.4

13

C-NMR: 181.8 ppm; 164.9 ppm; 65.9 ppm;

41.6 ppm; 36.5 ppm; 22.9 ppm

4.5

Melting point 75-76° C.

4.8

1

H-NMR: 4.6 ppm (2H); 4.4 ppm (2H); 3.3 ppm (4H);

1.35 ppm (3H); 1.25 ppm (3H)

4.9

1

H-NMR: 7.2 ppm (1H); 7.0 ppm (2H); 3.9 ppm (3H);

3.4 ppm (3H)

4.12

1

H-NMR: 7.1 ppm (1H); 6.9 ppm (2H); 4.9 ppm (2H);

3.4 ppm (3H); 2.5 ppm (1H)

4.15

1

H-NMR: 4.3 ppm (2H); 3.7 ppm (2H);

1.4-1.9 ppm (4H); 0.9-1.1 ppm (6H)

4.16

13

C-NMR: 170.0 ppm; 167.9 ppm; 136.0-143.2 ppm;

125.9 ppm; 55.2 ppm; 49.1 ppm

4.18

1

H-NMR: 3.95 ppm (2H); 3.85 ppm (2H); 3.6 ppm (2H);

1.4 ppm (6H)

4.20

1

H-NMR: 7.1 ppm (1H); 6.9 ppm (2H); 4.3 ppm (2H);

3.7 ppm (2H); 1.3 ppm (6H)

4.22

1

H-NMR: 4.0 ppm (2H); 3.7 ppm (2H); 1.6 ppm (9H)

4.23

13

C-NMR: 160.0 ppm; 122.6 ppm; 65.1 ppm; 63.6 ppm;

41.6 ppm

4.26

1

H-NMR: 4.3 ppm (4H); 3.6 ppm (2H); 1.8 ppm (4H);

1.6 ppm (2H); 1.0 ppm (6H); 0.9 ppm (3H)

4.29

1

H-NMR: 5.2 ppm (4H); 4.0 ppm (2H); 3.6 ppm (2H)

4.33

1

H-NMR: 3.95 ppm (6H); 3.7 ppm (2H); 1.3 ppm (3H)

4.38

13

C-NMR: 168.2 ppm; 94.3 ppm; 76.5 ppm; 64.9 ppm;

41.6 ppm

4.41

1

H-NMR: 7.2-8.0 ppm (4H); 4.35 ppm (2H);

4.25 ppm (2H); 3.7-3.9 ppm (2H); 1.2-1.4 ppm (9H)

4.43

1

H-NMR: 7.5 ppm (1H); 7.3 ppm (1H); 7.1 ppm (1H);

3.9 ppm (3H); 3.4 ppm (3H)

4.45

13

C-NMR: 168.5 ppm; 167.2 ppm; 136.1-143.0 ppm;

125.8 ppm; 81.7 ppm; 67.2 ppm; 40.7 ppm; 33.8 ppm

4.49

1

H-NMR: 3.95 ppm (2H); 3.65 ppm (2H); 1.6 ppm (18H)

4.50

1

H-NMR: 4.4 ppm (4H); 3.7 ppm (2H); 1.4 ppm (6H);

1.3 ppm (3H)

4.86

Melting point 141-142° C.

4.156

13

C-NMR: 169.0 ppm; 167.7 ppm; 142.8 ppm;

119.9 ppm; 67.3 ppm; 62.8 ppm; 45.6 ppm; 40.8 ppm;

40.6 ppm; 38.0 ppm; 36.5 ppm; 31.5 ppm; 31.3 ppm;

26.1 ppm; 21.0 ppm

4.157

13

C-NMR: 169.0 ppm; 167.6 ppm; 67.3 ppm; 63.7 ppm;

40.9 ppm; 18.4 ppm; −1.7 ppm

4.158

1

H-NMR: 4.6 ppm (2H); 3.75 ppm (2H); 3.6 ppm (2H);

1.65 ppm (2H); 0.5 ppm (2H); 0.0 ppm (9H)

4.159

1

H-NMR: 4.6 ppm (2H); 3.8 ppm (2H); 3.2 ppm (2H);

2.0 ppm (3H); 1.6-1.8 ppm (6H); 1.5 ppm (6H)

4.160

1

H-NMR: 4.55 ppm (2H); 3.7 ppm (2H); 3.0 ppm (2H);

0.0 ppm (9H)

4.161

1

H-NMR: 7.3-7.0 ppm (3H); 3.95 ppm (3H);

3.4 ppm (3H); 2.25 ppm (3H)

4.162

1

H-NMR: 7.1-7.4 ppm (5H); 4.35 ppm (2H);

3.75 ppm (2H); 1.2-1.4 ppm (6H)

4.163

1

H-NMR: 6.9-7.3 ppm (4H); 3.95 ppm (3H);

3.8 ppm (3H); 3.4 ppm (3H)

4.164

1

H-NMR: 5.2 ppm (4H); 4.0 ppm (2H); 3.65 ppm (2H)

4.165

1

H-NMR: 5.3 ppm (1H); 4.6 ppm (2H); 3.8 ppm (2H);

3.6 ppm (2H); 1.9-2.4 ppm (7H); 1.25 ppm (3H);

1.1 ppm (1 H); 0.8 ppm (3H)

4.166

1

H-NMR: 7.0 ppm (1H); 4.55 ppm (1H+2H);

3.75 ppm (2H); 0.8-1.9 ppm (16H)

4.167

13

C-NMR: 168.8 ppm; 168.4 ppm; 167.6 ppm;

167.1 ppm; 125-143 ppm; 80.5 ppm; 80.3 ppm;

67.3 ppm; 47.5 ppm; 44.8 ppm; 41.4 ppm; 40.7 ppm;

38.4 ppm; 37.0 ppm; 33.9 ppm; 27.3 ppm; 23.8 ppm;

19.6 ppm

4.168

13

C-NMR: 169.0 ppm; 167.7 ppm; 125-143 ppm;

67.7 ppm; 64.7 ppm; 41.4 ppm; 40.8 ppm

4.169

13

C-NMR: 168.4 ppm; 167.1 ppm; 84.8 ppm; 67.3 ppm;

47.9 ppm; 41.8 ppm; 40.8 ppm; 34.5 ppm; 33.4 ppm;

32.6 ppm; 29.2 ppm; 26.0 ppm; 25.7 ppm; 23.9 ppm

Example H13

Preparation of 3-amino-1-(β-chloroethoxy)-5-(2′,4′-dichlorophenoxy)thiatriazine (process d

4

)

6.5 g (0.013 mol) of 1-(β-chloroethoxy)-3,5-di(2′,4′-dichlorophenoxy)thiatriazine are dissolved in 100 ml of tetrahydrofuran. Thereafter, ammonia gas is passed in at 20° C. until the starting material can no longer be detected in a thin layer chromatogram (about 15 minutes). The reaction mixture is concentrated on a rotary evaporator and hexane is added to the still hot residue until crystallization starts. The crystals formed are filtered off with suction, washed with hexane and dried. 4.00 g (86.5% of theory) of the desired compound are obtained as crystals of melting point 141-142° C. Cl analysis: 29.3% (calculated 29.9%);

1

H-NMR (300 MHz, CDCl

3

): 7.2-7.5 ppm (3H), 6.6 and 6.3 ppm (2H), 3.9 ppm (2H), 3.6 ppm (2H).

Example H14

Preparation of 3-amino-1-isopropoxy-5-(2′,5′-difluorophenoxy)thiatriazine (process g)

0.50 g (0.0084 mol) of isopropanol is reacted with 0.37 g (0.0084 mol) of 55% sodium hydride in oil in 30 ml of tetrahydrofuran. 2.60 g (0.008 mol) of 3-amino-1-(β-chloroethoxy)-5-(2′,5′-difluorophenoxy)thiatriazine are added to the resulting suspension of the sodium isopropanolate at room temperature, and a slightly exothermic reaction takes place.

Extraction of the reaction mixture with water and ethyl acetate gives 2.0 g of crude product, which is recrystallized from a mixture of ethyl acetate/hexane 3/5. Yield of desired product 1.82 g (75% of theory) of melting point 163-164° C.

Analysis: C

11

H

12

F

2

N

4

O

2

S;

calculated.

found

[%]

[%]

C

43.7

43.3

H

4.0

4.0

N

18.5

18.4

1

H-NMR (300 MHz, CDCl

3

): 6.8-7.2 ppm (3H); 5.1-5.5 ppm (1H); 4.4 ppm (1H); 1.3 ppm (6H).

Example H15

Preparation of 3-dimethylamino-1-(β-chloroethoxy)-5-(2′-carboethoxyphenoxy)thiatriazine (process c

4

)

2.22 g (0.0064 mol) of 3-chloro-1-(β-chloroethoxy)-5-(2′-carboethoxyphenoxy)thiatriazine are dissolved in 30 ml of tetrahydrofuran. Dimethylamine is passed in at 0° C. until the conversion is complete, the reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the crude product is purified by means of chromatography (silica gel; ethyl acetate/hexane mixture). The desired product is obtained as an oil in a yield of 1.40 g (57% of theory). The

1

H-NMR spectrum is in agreement with the structure of the desired compound; mass spectrum: [M

+

]386.

Example H16

Preparation of 3-amino-5-(2,5-difluorophenoxy)-1-(3-hexyloxy)thiatriazine

2.1 g of trimethylamine solution (40% in water) are added to a mixture of 3.6 g of 3-amino-5-chloro-1-(3-hexyloxy)thiatriazine (0.014 mol), 70 ml of methylene chloride and 2.05 g of 2,5-difluorophenol (0.01 6 mol). The reaction mixture is stirred at 20° C. until the conversion is complete, and is then evaporated. Water is added to the resulting residue and the residue is filtered off with suction. The resulting solid is stirred in diethyl ether and filtered off, the clear ether solution is concentrated and pentane is added to the residue. The desired product precipitates in the form of white crystals of melting point 171-172° C.

The compounds listed in the following Table 5 can be prepared analogously to Examples H13 to H16.

TABLE 5

Compounds of the formula III

(III)

Comp.

No.

Process

R

7

R

3

R

2

5.1

d

4

—CH

2

CH

2

Cl

C

6

H

5

O—

—NH

2

5.2

d

4

—CH

2

CH

2

C

6

H

5

—N(CH

3

)C

4

H

9

(n)

5.3

q

—CH(CH

3

)

2

—NH

2

5.4

d

4

—CH

2

CH

2

Cl

—NH

2

5.5

d

5

—CH

2

CH

2

Cl

—NH

2

5.6

d

4

—CH

2

CH

2

Cl

C

6

F

5

O—

—N(CH

3

)

2

5.7

q

—NH

2

5.8

q

—NH

2

5.9

C

6

F

5

O—

—NH

2

5.10

d

4

—CH

2

CH

2

C

6

H

5

5.11

d

4

—CH

2

CH

2

Cl

C

6

H

5

O—

—N(CH

3

)

2

5.12

C

6

F

5

O—

—NH

2

5.13

d

4

—CH

2

CH

2

Cl

C

6

F

5

O—

—NH

2

5.14

q

—NH

2

5.15

d

4

—CH

2

CH

2

Cl

—NHC(CH

3

)

3

5.16

C

6

F

5

O—

—NH

2

5.17

d

4

—CH

2

CH

2

Cl

5.18

C

6

F

5

O—

—NH

2

5.19

q

—NH

2

5.20

—CH

2

CH

2

Cl

—NH

2

5.21

—NH

2

5.22

c

4

—CH

2

CH

2

Cl

—N(CH

3

)

2

5.23

d

4

—CH

2

CH

2

Cl

—N(CH

3

)

2

5.24

—CH

2

CH

2

Cl

—NH

2

5.25

—NH

2

5.26

C

6

F

5

O—

—NH

2

5.27

C

6

F

5

O—

—NH

2

5.28

d

4

—CH

2

CH

2

Cl

—NH

2

5.29

—CH

2

CH

2

Cl

5.30

q

C

6

F

5

O—

—NH

2

5.31

d

4

—NH

2

5.32

—CH

2

CH

2

Cl

—NH

2

5.33

—CH

2

CH═CH

2

C

6

F

5

O—

—NH

2

5.34

C

6

F

5

O—

—NH

2

5.35

d

4

5.36

—(CH

2

)

6

CH

3

C

6

F

5

O—

—NH

2

5.37

—NH

2

5.38

d

4

C

6

F

5

O—

—NH

2

5.39

—NH

2

5.40

—CH

2

CH

2

NO

2

—NH

2

5.41

—CH

2

C

6

F

5

—NH

2

5.42

d

4

—NH

2

5.43

—NH

2

5.44

—NH

2

5.45

q

—CH

3

—NHCH

2

CH

2

CH

3

5.46

q

C

6

F

5

O—

—NH

2

5.47

q

C

6

F

5

O—

—NH

2

5.48

d

4

—CH

2

CH

2

Cl

—NH

2

5.49

—CH

2

CH

2

Cl

C

6

F

5

O—

5.50

—NH

2

5.51

q

—CH

3

—N(CH

3

)

2

5.52

q

C

6

F

5

O—

—NH

2

5.53

C

6

F

6

O—

—NH

2

5.54

q

—CH

3

—NH

2

5.55

d

4

—CH

2

CH

2

Cl

—N(CH

3

)

2

5.56

C

6

F

5

O—

—NH

2

5.57

C

6

F

5

O—

—NH

2

5.58

q

—NH

2

5.59

q

C

6

F

5

O—

—NH

2

5.60

d

4

—CH

2

CH

2

Cl

—NHCH

2

CH

2

CH

3

5.61

C

6

F

5

O—

—NH

2

5.62

C

6

F

5

O—

—NH

2

5.63

C

6

F

5

O—

—NH

2

5.64

q

—CH

3

—NHCH

2

CH

2

CH

3

5.65

q

C

6

F

5

O—

—NH

2

5.66

—CH

2

CH

2

COOC

2

H

5

C

6

F

5

O—

—NH

2

5.67

d

4

—NH

2

5.68

—CH

2

C═CH

C

6

F

5

O—

—NH

2

5.69

C

6

F

5

O—

—NH

2

5.70

C

6

F

5

O—

—NH

2

5.71

q

—CH

3

—NH

2

5.72

d

4

—NH

2

5.73

c

4

—NH

2

5.74

d

4

—NHCH

3

5.75

q

—NH

2

5.76

C

6

F

5

O—

—NH

2

5.77

—CH

2

CH

2

CCl

3

C

6

F

5

O—

—NH

2

5.78

q

C

6

F

5

O—

—NH

2

5.79

C

6

F

5

O—

—NH

2

5.80

C

6

F

5

O—

—NH

2

5.81

—NH

2

5.82

C

6

F

5

O—

—NH

2

5.83

q

C

6

F

5

O—

—NH

2

5.84

q

C

6

F

5

O—

—NH

2

5.85

—CH

2

-Adamantyl

C

6

F

5

O—

—NH

2

5.86

q

—C

6

F

5

O—

—NH

2

5.87

C

6

F

5

S—

—NH

2

5.88

d

4

C

6

F

5

S—

—NH

2

5.89

d

4

—CH

2

CH

2

Cl

C

6

F

5

S—

—NH

2

5.90

q

C

6

F

5

O—

—NH

2

5.91

C

6

F

5

O—

—NH

2

5.92

q

C

6

F

5

O—

—NH

2

5.93

C

6

F

5

O—

—NH

2

5.94

c

4

5.95

C

6

F

5

O—

—NH

2

5.96

q

—CH

2

CH

2

OCH

3

—NH

2

5.97

—NHC

4

H

9

(n)

5.98

d

4

C

6

F

5

O—

—NH

2

5.99

C

6

F

5

O—

—NH

2

5.100

C

6

F

5

S—

—NH

2

5.101

C

6

F

5

O—

—NH

2

5.102

q

—CH

2

CH

2

F

—NH

2

5.103

q

—NH

2

5.104

C

6

F

5

O—

—NH

2

5.105

—(CH

2

)

7

CH

3

—NHCH

3

5.106

C

6

F

5

O—

—NH

2

5.107

q

—C

2

H

5

—NH

2

5.108

q

—NH

2

5.109

—CH(CH

3

)C

2

H

5

—NH

2

5.110

q

—C(CH

3

)

3

—NH

2

5.111

C

6

F

5

O—

—NH

2

5.112

C

6

F

5

O—

—NH

2

5.113

q

—CH

3

—NHC(CH

3

)

3

5.114

C

6

F

5

O—

—NH

2

5.115

C

6

F

5

O—

—NH

2

5.116

q

—NH

2

5.117

C

6

F

5

O—

—NH

2

5.118

C

6

F

5

O—

—NH

2

5.119

q

—CH

3

—NH

2

5.120

q

C

6

F

5

O—

—NH

2

5.121

d

4

—NHCH(CH

3

)CH

2

OCH

3

5.122

d

4

—NH

2

5.123

C

6

F

5

O—

—NH

2

5.124

C

6

F

5

O—

—NH

2

5.125

q

—C

2

H

5

—NH

2

5.126

d

4

—NH

2

5.127

C

6

F

5

O—

—NH

2

5.128

C

6

F

5

O—

—NH

2

5.129

q

—NH

2

5.130

q

—NH

2

5.131

q

C

6

F

5

O—

—NH

2

5.132

d

4

C

6

F

5

O—

—NH

2

5.133

d

4

—NH

2

5.134

C

6

F

5

O—

—NH

2

5.135

q

C

6

F

5

O—

—NH

2

5.136

C

6

F

5

O—

—NH

2

5.137

C

6

F

5

O—

—NH

2

5.138

d

4

—NHCH

3

5.139

C

6

F

5

O—

—NH

2

5.140

C

6

F

5

O—

—NH

3

5.141

q

C

6

F

5

O—

—NH

2

5.142

C

6

F

5

O—

—NH

2

5.143

q

—NH

2

5.144

d

4

—NH

2

5.145

q

C

6

F

5

O—

—NH

2

5.146

q

C

6

F

5

O—

—NH

2

5.147

d

4

—NH

2

5.148

q

C

6

F

5

O—

—NH

2

5.149

—NH

2

5.150

d

4

C

6

F

5

S—

—NH

2

5.151

d

4

C

6

F

5

O—

—NHC

2

H

5

5.152

d

4

C

6

F

5

O—

—NH

2

5.153

d

4

C

6

F

5

O—

—NH

2

5.154

q

C

6

F

5

O—

—NH

2

5.155

C

6

F

5

O—

—NH

2

5.156

q

—(CH

2

)

4

CH

3

—NH

2

5.157

q

—NH

2

5.158

C

6

F

5

O—

—NH

2

5.159

—NH

2

5.160

q

—CH

2

CH

2

SC

2

H

5

—NH

2

5.161

d

4

—CH

2

CH

2

Si(CH

3

)

3

C

6

F

5

O—

—NH

2

5.162

q

—(CH

2

)

9

CH

3

—NH

2

5.163

C

6

F

5

O—

—NH

2

5.164

C

6

F

5

O—

—NH

2

5.165

C

6

F

5

O—

—NH

2

5.166

C

6

F

5

O—

—NH

2

5.167

—CH

2

CH

2

Cl

—NH

2

5.168

q

—(CH

2

)

2

(CF

2

)

3

CF

3

—NH

2

5.169

C

6

F

5

O—

—NH

2

5.170

—CH

2

CH(C

6

H

5

)

2

C

6

F

5

O—

—NH

2

5.171

C

6

F

5

O—

—NH

2

5.172

q

—NH

2

5.173

C

6

F

5

O—

—NH

2

5.174

d

4

—CH

2

CH

2

Cl

—NH

2

5.175

C

6

F

5

O—

—NH

2

5.176

q

C

6

F

5

O—

—NH

2

5.177

d

4

—CH

2

CH

2

Cl

—NH

2

5.178

d

4

—CH

2

CH

2

Cl

—NHCH

2

CH

2

CH

3

5.179

—NHC

4

H

9

(n)

5.180

d

4

C

6

F

5

O—

—NH

2

5.181

C

6

F

5

O—

—NH

2

5.182

d

4

—CH

2

CH

2

Cl

—NHCH(CH

3

)

2

5.183

d

4

—CH

2

CH

2

Cl

—N(C

2

H

5

)

2

5.184

d

4

—CH

2

CH

2

Cl

—NH

2

5.185

C

6

F

5

O—

—NH

2

5.186

C

6

F

5

O—

—NH

2

5.187

C

6

F

5

O—

—NH

2

5.188

d

4

—CH

2

CH

2

Cl

5.189

—CH

2

CH

2

Cl

—NH

2

5.190

—CH

2

CH

2

Cl

—NH

2

5.191

C

6

F

5

O—

—NH

2

5.192

d

4

—CH

2

CH

2

Cl

—NH

2

5.193

d

4

—CH

2

CH

2

Cl

—N(CH

3

)

2

5.194

C

6

F

5

O—

—NH

2

5.195

q

C

6

F

5

O—

—NH

2

5.196

C

6

F

5

O—

—NH

2

5.197

q

C

6

F

5

O—

—NH

2

5.198

C

6

F

5

O—

—NH

2

5.199

—CH

2

CH

2

Cl

—NH

2

5.200

—CH

2

CH

2

Cl

—NH

2

5.201

C

6

F

5

O—

—NH

2

5.202

C

6

F

5

O—

—NH

2

5.203

—CH

2

CH

2

Cl

—NH

2

5.204

—NH

2

5.205

—NH

2

5.206

—CH

2

CH

2

Cl

—NH

2

5.207

C

6

F

5

O—

—NH

2

5.208

—NH

2

5.209

—NH

2

5.210

—CH

2

CH

2

Cl

—NH

2

5.211

—CH

2

CH

2

Cl

—NH

2

5.212

—CH

2

CH

2

Cl

—NH

2

5.213

—NH

2

5.214

—NH

2

5.215

—CH

2

CH

2

Cl

—NH

2

5.216

—CH

2

CH

2

Cl

—NH

2

5.217

—CH

2

CH

2

Cl

—NH

2

5.218

—CH

2

CH

2

Cl

—NH

2

5.219

—NH

2

5.220

—CH

2

CH

2

Cl

—NH

2

5.221

—CH

2

CH

2

Cl

—NH

2

5.222

—CH

2

CH

2

Cl

—NH

2

5.223

—CH

2

CH

2

Cl

—NH

2

5.224

—CH

2

CH

2

Cl

—NH

2

5.225

—NH

2

5.226

—CH

2

CH

2

Cl

—NH

2

5.227

—NH

2

5.228

—CH

2

CH

2

Cl

—NH

2

5.229

—CH

2

CH

2

Cl

—NH

2

5.230

—CH

2

CH

2

Cl

—NH

2

5.231

—CH

2

CH

2

Cl

—NH

2

5.232

—CH

2

CH

2

Cl

—NH

2

5.233

—CH

2

CH

2

Cl

—NH

2

5.234

—CH

2

CH

2

Cl

—NH

2

5.235

—CH

2

CH

2

Cl

—NH

2

5.236

—CH

2

CH

2

Cl

—NH

2

5.237

—NH

2

5.238

—NH

2

5.239

—CH

2

CH

2

Cl

—NH

2

5.240

—CH

2

CH

2

Cl

—NH

2

5.241

—NH

2

5.242

—CH

2

CH

2

Cl

—NH

2

5.243

—CH

2

CH

2

Cl

—NH

2

5.244

—CH

2

CH

2

Cl

—NH

2

5.245

—CH

2

CH

2

Cl

—NH

2

5.246

—CH

2

CH

2

Cl

—NH

2

5.247

—CH

2

CH

2

Cl

—NH

2

5.248

—CH

2

CH

2

Cl

—NH

2

5.249

—CH

2

CH

2

Cl

—NH

2

5.250

—CH

2

CH

2

Cl

—NH

2

5.251

—CH

2

CH

2

Cl

—NH

2

5.252

—CH

2

CH

2

Cl

—NH

2

5.253

—CH

2

CH

2

Cl

—NH

2

5.254

—CH

2

CH

2

Cl

—NH

2

5.255

—CH

2

CH

2

Cl

—NH

2

5.256

—CH

2

CH

2

Cl

—NH

2

5.257

—CH

2

CH

2

Cl

—NH

2

5.258

—CH

2

CH

2

Cl

—NH

2

5.259

—CH

2

CH

2

Cl

—NH

2

5.260

—CH

2

CH

2

Cl

—NH

2

5.261

—CH

2

CH

2

Cl

—NH

2

5.262

—CH

2

CH

2

Cl

—NH

2

5.263

—CH

2

CH

2

Cl

—NH

2

5.264

—CH

2

CH

2

Cl

—NH

2

5.265

—CH

2

CH

2

Cl

—NH

2

5.266

—CH

2

CH

2

Cl

—NH

2

5.267

—CH

2

CH

2

Cl

—NH

2

5.268

—CH

2

CH

2

Cl

—NH

2

5.269

—CH

2

CH

2

Cl

—NH

2

5.270

—CH

2

CH

2

Cl

—NH

2

5.271

—CH

2

CH

2

Cl

—NH

2

5.272

—CH

2

CH

2

Cl

—NH

2

5.273

—CH

2

CH

2

Cl

—NH

2

5.274

—CH

2

CH

2

Cl

—NH

2

5.275

—CH

2

CH

2

Cl

—NH

2

5.276

—CH

2

CH

2

Cl

—NH

2

5.277

—CH

2

CH

2

Cl

—NH

2

5.278

—CH

2

CH

2

Cl

—NH

2

5.279

—CH

2

CH

2

Cl

—NH

2

5.280

—CH

2

CH

2

Cl

—NH

2

5.281

—CH

2

CH

2

Cl

—NH

2

5.282

—CH

2

CH

2

Cl

—NH

2

5.283

—CH

2

CH

2

Cl

—NH

2

5.284

—CH

2

CH

2

Cl

—NH

2

5.285

—CH

2

CH

2

Cl

—NH

2

5.286

C

6

F

5

O—

—NH

2

5.287

C

6

F

5

O—

—NH

2

5.288

C

6

F

5

O—

—NH

2

5.289

C

6

F

5

O—

—NH

2

5.290

C

6

F

5

O—

—NH

2

5.291

C

6

F

5

O—

—NH

2

5.292

C

6

F

5

O—

—NH

2

5.293

C

6

F

5

O—

—NH

2

5.294

C

6

F

5

O—

—NH

2

5.295

C

6

F

5

O—

—NH

2

5.296

C

6

F

5

O—

—NH

2

5.297

C

6

F

5

O—

—NH

2

5.298

C

6

F

5

O—

—NH

2

5.299

C

6

F

5

O—

—NH

2

5.300

C

6

F

5

O—

—NH

2

5.301

C

6

F

5

O—

—NH

2

5.302

C

6

F

5

O—

—NH

2

5.303

C

6

F

5

O—

—NH

2

5.304

C

6

F

5

O—

—NH

2

5.305

C

6

F

5

O—

—NH

2

5.306

C

6

F

5

O—

—NH

2

5.307

C

6

F

5

O—

—NH

2

5.308

C

6

F

5

O—

—NH

2

5.309

C

6

F

5

O—

—NH

2

5.310

C

6

F

5

O—

—NH

2

5.311

C

6

F

5

O—

—NH

2

5.312

C

6

F

5

O—

—NH

2

5.313

C

6

F

5

O—

—NH

2

5.314

C

6

F

5

O—

—NH

2

5.315

d

4

—(CH

2

)

3

Si(CH

3

)

3

C

6

F

5

O—

—NH

2

5.316

d

4

C

6

F

5

O—

—NH

2

5.317

c

5

C

6

F

5

O—

—NH

2

5.318

c

5

—NH

2

5.319

d

4

C

6

F

5

O—

—NH

2

5.320

d

4

C

6

F

5

O—

—NH

2

5.321

d

4

—CH

2

Si(CH

3

)

3

C

6

F

5

O—

—NH

2

5.322

d

4

C

6

F

5

O—

—NHC

2

H

5

5.323

d

4

C

6

F

5

O—

—NHCH

3

5.324

d

4

C

6

F

5

O—

—NH

2

5.325

d

4

C

6

F

5

O—

—NH

2

5.326

d

4

C

6

F

5

O—

—NH

2

5.327

d

4

C

6

F

5

O—

—NH

2

5.328

d

4

C

6

F

5

O—

—NH

2

5.329

d

4

—CH(CH

3

)—Si(CH

3

)

3

C

6

F

5

O—

—NH

2

5.330

q

—CH

3

C

6

F

5

O—

—NH

2

5.331

—CH(CH

3

)COOCH

3

C

6

F

5

O—

—NH

2

5.332

c

5

C

6

F

5

O—

—NH

2

5.333

d

4

—CH

2

CH

2

Cl

—NH

2

5.334

—NH

2

5.335

q

—CH

2

CH

2

Cl

CF

3

CH

2

O—

—NH

2

5.336

q

—CH

2

CH

2

Cl

(CF

3

)

2

CHO—

—NH

2

5.337

q

—CH

2

CH

2

Cl

CF

3

CCl

2

CH

2

O—

—NH

2

5.338

d

4

—NH

2

5.339

c

5

—CH[CH

2

CH(CH

3

)

2

]

2

C

6

F

5

O—

—NH

2

5.340

c

5

—NH

2

5.341

d

4

—NH

2

5.342

d

4

—NH

2

5.343

d

4

—CH

2

Si(CH

3

)

3

—NH

2

5.344

d

4

C

6

F

5

O—

—NH

2

5.345

d

4

C

6

F

5

O—

—NH

2

5.346

d

4

C

6

F

5

O—

—NH

2

5.347

C

6

F

5

O—

—NH

2

5.348

C

6

F

5

O—

—NH

2

5.349

d

4

C

6

F

5

O—

—NH

2

5.350

d

4

C

6

F

5

O—

—NH

2

5.351

d

4

C

6

F

5

O—

—NH

2

5.352

d

4

C

6

F

5

O—

—NH

2

5.353

C

6

F

5

O—

—NH

2

5.354

C

6

F

5

O—

—NH

2

5.355

d

4

C

6

F

5

O—

—NH

2

5.356

d

4

C

6

F

5

O—

—NH

2

5.357

d

4

C

6

F

5

O—

—NH

2

5.358

d

4

C

6

F

5

O—

—NH

2

5.359

d

4

C

6

F

5

O—

—NH

2

5.360

d

4

C

6

F

5

O—

—NH

2

5.361

C

6

F

5

O—

—NH

2

5.362

C

6

F

5

O—

—NH

2

5.363

d

4

C

6

F

5

O—

—NH

2

5.364

d

4

C

6

F

5

O—

—NH

2

5.365

C

6

F

5

O—

—NH

2

5.366

d

4

—CH

2

CH

2

Cl

—NH

2

5.367

C

6

F

5

O—

—NH

2

5.368

C

6

F

5

O—

—NH

2

5.369

d

4

C

6

F

5

O—

—NH

2

5.370

—CH

2

CH

2

C

6

F

5

C

6

F

5

O—

—NH

2

5.371

C

6

F

5

O—

—NH

2

5.372

C

6

F

5

O—

—NH

2

5.373

C

6

F

5

O—

—NH

2

5.374

C

6

F

5

O—

—NH

2

5.375

d

4

—NH

2

5.376

d

4

—NH

2

5.377

d

4

—NH

2

Physical data of compounds in Table 5:

Comp. No.

Physical data

5.1

Melting point 152-153° C.

5.2

1

H-NMR: 6.8-7.3 ppm (8H); 3.7-4.0 ppm (2H);

3.2-3.6 ppm (2H); 2.8-3.0 ppm (5H); 0.8-1.6 ppm (7H)

5.3

Melting point 163-164° C.

5.4

Melting point 167-168° C.

5.5

Melting point 141-142° C.

5.6

1

H-NMR: 3.8-4.0 ppm (2H); 3.6 ppm (2H);

3.2 ppm (3H); 3.0 ppm (3H)

5.7

Melting point 145-146° C.

5.8

Melting point 148-149° C.

5.10

1

H-NMR: 6.8-7.3 ppm (8H); 5.3-5.5 ppm (1H);

4.0-4.3 ppm (1H); 3.8 ppm (2H); 2.9 ppm (2H)

5.11

1

H-NMR: 7.1-7.4 ppm (5H); 3.9 ppm (2H);

3.6 ppm (2H); 3.13 ppm (3H); 3.05 ppm (3H)

5.13

Melting point 127-128° C.

5.14

Melting point 140-141° C.

5.15

1

H-NMR: 6.5-7.2 ppm (3H); 5.3 ppm (1H);

3.6-4.0 ppm (4H); 1.45 ppm (9H)

5.17

1

H-NMR: 7.1-7.5 ppm (3H); 3.6-4.0 ppm (12H)

5.19

Melting point 179-180° C.

5.22

1

H-NMR: 7.2-8.0 ppm (4H); 4.3 ppm (2H);

3.8-4.1 ppm (2H); 3.6 ppm (2H); 3.1 ppm (3H);

3.0 ppm (3H); 1.3 ppm (3H)

5.23

1

H-NMR: 6.9-7.2 ppm (3H); 3.8-4.0 ppm (2H);

3.6 ppm (2H); 3.15 ppm (3H); 3.0 ppm (3H)

5.28

Melting point 130-131° C.

5.30

Melting point 207-208° C.

5.31

Melting point 159-160° C. (decomposition)

5.35

1

H-NMR: 6.8-7.4 ppm (8H); 5.5 ppm (1H);

4.7 ppm (2H); 4.2 ppm (1H); 1.9 ppm (4H);

1.4-1.7 ppm (4H)

5.38

Melting point 163-164° C.

5.42

Melting point 181-182° C.

5.45

Melting point 98-99° C.

5.46

Melting point 147-148° C.

5.47

Melting point 125-126° C.

5.48

Melting point 161-162° C.

5.51

Melting point 87-88° C.

5.52

Melting point 138-139° C.

5.54

Melting point 215-216° C.

5.55

1

H-NMR: 6.8-7.1 ppm (3H); 3.8-4.0 ppm (2H);

3.6 ppm (2H); 3.15 ppm (3H); 3.0 ppm (3H)

5.58

Melting point 202-203° C.

5.59

Melting point 123-124° C.

5.60

1

H-NMR: 6.9-7.2 ppm (3H); 3.7-4.0 ppm (2H);

3.6 ppm (2H); 3.4 ppm (2H); 1.6 ppm (2H);

0.9 ppm (3H)

5.64

Melting point 112-113° C.

5.65

Melting point 103-104° C.

5.67

Melting point 176-177° C.

5.71

Melting point 204-206° C. (decomposition)

5.72

Melting point 178-179° C.

5.73

Melting point 173-174° C.

5.74

1

H-NMR: 6.8-7.3 ppm (4H); 4.3 ppm (1H);

4.0 ppm (1H); 3.8 ppm (3H); 2.8-3.0 ppm (3H);

1.2-2.2 ppm (12H)

5.75

Melting point 167-168° C.

5.76

Melting point 175-176° C. (decomposition)

5.78

Melting point 165-166° C.

5.83

Oil

5.84

Melting point 109-110° C.

5.85

Melting point 175-176° C. (decomposition)

5.86

Melting point 165-166° C.

5.88

Melting point 115-116° C.

5.89

Melting point 91-92° C.

5.90

Melting point 179-180° C. (decomposition)

5.92

Melting point 212-213° C.

5.94

1

H-NMR: 6.9-7.3 ppm (4H); 3.8-4.6 ppm (6H);

3.8 ppm (3H); 0.7-2.9 ppm (22H)

5.96

Melting point 108-109° C.

5.98

Melting point 138-139° C.

5.101

Melting point 182-183° C.

5.102

Melting point 145-146° C.

5.103

Melting point 183-185° C.

5.107

Melting point 190-191° C.

5.108

Melting point 204-205° C.

5.110

Melting point 124-125° C.

5.113

1

H-NMR: 6.5-7.2 ppm (3H); 5.3 ppm (1H);

3.4 ppm (3H); 1.45 ppm (9H)

5.114

Melting point 137-138° C.

5.116

Melting point 216-217° C.

5.117

Melting point 161-162° C.

5.119

Melting point 194-196° C. (decomposition)

5.120

Melting point 156-157° C.

5.121

1

H-NMR: 7.3 ppm (5H); 7.1 ppm (1H); 6.9 ppm (2H);

5.6 ppm (1H); 4.7 ppm (2H); 4.2 ppm (1H);

3.2-3.4 ppm (5H); 1.2 ppm (3H)

5.122

Melting point 103-104° C.

5.125

Melting point 162-163° C.

5.126

Melting point 197-198° C.

5.127

Melting point 118-119° C.

5.129

Melting point 140-141° C.

5.130

Melting point 167-168° C.

5.131

Melting point 140-141° C.

5.132

Melting point 147-148° C.

5.133

Melting point 139-140° C.

5.135

13

C-NMR: 166.0 ppm; 165.2 ppm; 75.6 ppm; 68.5 ppm;

66.2 ppm; 27.8 ppm; 25.6 ppm; 22.9 ppm

5.138

Melting point 132-133° C.

5.141

Melting point 115-116° C.

5.143

Melting point 105-106° C.

5.144

Melting point 183-184° C.

5.145

Melting point 106-107° C.

5.146

Melting point 182-184° C.

5.147

Melting point 198-199° C.

5.148

Melting point 108-109° C.

5.150

Melting point 115-116° C.

5.151

Melting point 122-123° C.

5.152

Melting point 122-123° C.

5.153

Oil

5.154

Melting point 178-180° C. (decomposition)

5.156

Melting point 148-149° C.

5.157

Melting point 162-163° C.

5.160

Melting point 103-104° C.

5.161

Melting point 120-121° C.

5.162

Melting point 117-118° C.

5.168

Melting point 127-128° C.

5.172

Melting point 148-149° C.

5.174

Melting point 125-126° C.

5.176

Melting point 139-140° C.

5.177

1

H-NMR: 8.3 ppm (1H); 7.4 ppm (1H); 7.2 ppm (1H);

6.8 ppm (1H); 6.5 ppm (1H); 3.9 ppm (2H);

3.6 ppm (2H); 2.5 ppm (3H)

5.178

1

H-NMR: 7.1-7.4 ppm (3H); 3.8-4.0 ppm (2H);

3.6 ppm (2H); 3.3 ppm (2H); 1.4-1.7 ppm (2H);

0.8-1.0 ppm (3H)

5.180

Melting point 123-124° C.

5.182

Melting point 138-140° C.

5.183

1

H-NMR: 7.7 ppm (1H); 7.1-7.3 ppm (2H);

5.5 ppm (1H); 3.6-4.2 ppm (4H); 3.5 ppm (2H);

3.2 ppm (2H); 1.6 ppm (3H); 1.2 ppm (3H);

0.9 ppm (3H)

5.184

Melting point 146-147° C.

5.188

Melting point 123-124° C.

5.192

Melting point 182-183° C.

5.193

1

H-NMR: 7.7 ppm (1H); 7.2-7.3 ppm (2H);

5.5 ppm (1H); 3.6-4.2 ppm (4H); 3.1 ppm (3H);

2.9 ppm (3H); 1.6 ppm (3H)

5.195

Melting point 167-168° C.

5.197

Melting point 177-178° C.

5.207

Melting point 157-158° C.

5.315

Melting point 111-112° C.

5.316

Melting point 145-146° C.

5.317

Melting point 137-139° C.

5.318

Melting point 171-173° C.

5.319

Melting point 146-147° C. (decomposition)

5.320

Melting point 175-176° C. (decomposition)

5.321

Melting point 179-180° C.

5.322

Melting point 210-211° C. (decomposition)

5.323

solid

5.324

Melting point 112° C. (decomposition)

5.325

Melting point 116° C. (decomposition)

5.326

Melting point 118-119° C.

5.327

Melting point 148-149° C.

5.328

Melting point 129-130° C. (decomposition)

5.329

Melting point 157-158° C. (decomposition)

5.330

Melting point 142-143° C.

5.332

Melting point 142-143° C.

5.333

Melting point 141-142° C.

5.334

Melting point 124-125° C.

5.335

Melting point 137-140° C.

5.336

Resin; MS: [M

+

] 360/362

5.337

Melting point 162-163° C.

5.338

Melting point 181-182° C.

5.339

Melting point 112-114° C.

5.340

Melting point 171-172° C.

5.341

Melting point 154-155° C.

5.342

Melting point 178-179° C.

5.343

Melting point 223-224° C.

5.344

Melting point 163-164° C.

5.345

Melting point 167-168° C.

5.346

Melting point 117-118° C.

5.349

Melting point 151-152° C.

5.350

Melting point 146-147° C.

5.351

Melting point 124-125° C.

5.352

Melting point 134-135° C.

5.355

Melting point 164-165° C.

5.356

Melting point 145-146° C.

5.357

Melting point 186-187° C.

5.358

Melting point 169-170° C.

5.359

Melting point 164-165° C.

5.360

Melting point 136-137° C.

5.363

Melting point 183-184° C.

5.364

Melting point 118-119° C.

5.366

Melting point 131-132° C. (decomposition)

5.369

Melting point 146-147° C.

5.375

Melting point 188-189° C.

5.376

Melting point >225° C.

5.377

Melting point 156-157° C.

Example H17

Preparation of 3-amino-1-dipropylamino-5-(2′,5′-difluorophenoxy)thiatriazine

1.60 g (0.005 mol) of 3-amino-1-(β-chloroethoxy)-5-(2′,5′-difluorophenoxy)thiatriazine are stirred in 20 ml of toluene with 0.53 9 (0.00525 mol) of dipropylamine at 70° C. for 3.5 hours. After the reaction mixture has cooled, it is extracted with ethyl acetate and water. On concentration of the reaction mixture on a rotary evaporator, the desired product crystallizes out. It is filtered off with suction, washed and dried. Yield 1.42 g (83% of theory); melting point 184-185° C.

Analysis: C

14

H

19

F

2

N

5

OS;

calculated

found

[%]

[%]

C

48.97

48.92

H

5.58

5.61

N

20.39

20.24

Example H18

Preparation of 3-amino-1-decahydroquinolinyl-5-(2′,6′-difluorophenoxy)thiatriazine

1.00 g (0.0027 mol) of 1-(trans-2′-chlorocyclohexanolyl)-3-amino-5-(2′,6′-difluorophenoxy)thiatriazine is heated at 80-90° C. with 0.49 g (0.0035 mol of decahydroquinoline (cis/trans mixture) in 20 ml of toluene until the conversion is complete. Thereafter, the mixture is concentrated on a rotary evaporator, the residue is dissolved in ethyl acetate, the clouding formed is filtered off with suction and the filtrate is concentrated. Recrystallization of the resulting residue from a mixture of ethyl acetate/hexane gives 0.85 g (82% of theory) of the desired product of melting point 194-195° C. (decomposition). The

1

H— and

13

C-NMR spectra are in agreement with the structure of the desired product.

Example H19

Preparation of 3-amino-5-pentafluorophenoxy-1-(piperidin-1-yl)thiatriazine

8.3 ml of 2N sodium hydroxide solution (0.0166 mol) and 2.2 g of trimethylamine solution (40% in water) (0.015 mol) are added to a mixture of 3.5 9 of 3-amino-5-chloro-1-(piperidin-1-yl)thiatriazine (0.015 mol) and 3.0 g of pentafluorophenol (0.0165 mol) in 100 ml of methylene chloride. After the mixture has been stirred for 20 hours, the organic phase is dried over sodium sulfate and filtered over silica gel, with subsequent elution with a 50/50 hexane/ethyl acetate mixture. After the collected fractions have been evaporated and the residue has been stirred in pentane, the desired product is isolated as slightly yellowish crystals of melting point 104-105° C. (decomposition).

The compounds listed in the following Table 6 can be prepared analogously to Examples H17 to H19.

TABLE 6

Compounds of the formula II

(II)

Comp.

No.

R

1

R

3

R

2

Physical data

6.1

—NHCH

2

CH

2

CH

3

—NH

2

Melting point 132-133° C.

6.2

—N(CH

3

)

2

1

H-NMR: 6.8- 7.1 ppm (3H); 5.6-5.8 ppm (2H); 3.0-5.5 ppm (10 H); 2.2 ppm (2H)

6.3

—NH

2

Melting point 194-195° C. (decom- position)

6.4

—NH

2

Melting point 121-122° C.

6.5

—NH

2

Melting point 170-171° C.

6.6

C

6

F

5

O—

—NH

2

13

C-NMR: 165.7 ppm; 165.0 ppm; 63.7 ppm; 44.8 ppm; 43.3 ppm; 34.1 ppm; 32.2 ppm; 31.5 ppm; 24.5 ppm.

6.7

C

6

F

5

O—

—NH

2

Melting point 201-202° C.

6.8

C

6

F

5

O—

—NH

2

Melting point 162-163° C.

6.9

C

6

F

5

O—

—NH

2

Melting point 147-148° C. (decom- position)

6.10

C

6

F

5

O—

—NH

2

13

C-NMR: 165.7 ppm. 165.0 ppm; 63.7 ppm. 45.1 ppm; 43.6 ppm; 34.4 ppm; 32.1 ppm; 31.6 ppm; 24.7 ppm

6.11

—NH

2

Melting point 167-168° C.

6.12

—NH

2

Melting point 148-149° C.

6.13

C

6

F

5

S—

—NH

2

6.14

C

6

F

5

O—

—NH

2

Melting point 185-186° C. (decom- position)

6.15

C

6

F

5

O—

—NH

2

Melting point 102-103° C.

6.16

—N(CH

2

CH

2

CN)

2

C

6

F

5

O—

—NH

2

13

C-NMR: 165.8 ppm; 164.7 ppm; 118.5 ppm; 117.4 ppm; 49.6 ppm; 43.0 ppm; 18.6 ppm; 17.4 ppm

6.17

—NHC

6

H

11

(c)

C

6

F

5

O—

—NH

2

Melting point 136-137° C.

6.18

—NH

2

Melting point 189-190° C. (decom- position)

6.19

—NH

2

6.20

—NH

2

6.21

—N(n-C

3

H

7

)

2

C

6

F

5

O—

—NH

2

Melting point

111-112° C.

6.22

C

6

F

5

O—

—NH

2

Melting point 137-138° C.

6.23

—NH

2

Melting point 190-191° C.

6.24

C

6

F

5

O—

—NH

2

6.25

C

6

F

5

O—

—NH

2

6.26

C

6

F

5

O—

—NH

2

6.27

C

6

F

5

O—

—NH

2

Melting point 150-151° C. (decom- position)

6.28

—NH

2

Melting point 137-139° C.

6.29

—NH

2

Melting point 128-129° C.

6.30

C

6

F

5

O—

—NH

2

Melting point 161-162° C.

6.31

C

6

F

5

O—

—NH

2

Melting point 173-174° C.

6.32

C

6

F

5

O—

—NH

2

6.33

—NH

2

6.34

C

6

F

5

O—

—NH

2

Melting point 180-181° C. (decom- position)

6.35

—NH

2

6.36

—N[CH(CH

3

)

2

]

2

—NH

2

6.37

C

6

F

5

O—

—NH

2

Melting point 183-184° C. (decom- position)

6.38

—N(C

2

H

5

)

2

—NH

2

6.39

—N(C

2

H

5

)C

4

H

9

(n)

—NHCH

3

6.40

—NH

2

Melting point 208-209° C.

6.41

C

6

F

5

O—

—NH

2

Melting point 162-163° C.

6.42

C

6

F

5

O—

—NH

2

MS: [M

+

+ H, 45%] 450. [M

+

, 40% ]449

6.43

—N(CH

3

)

2

—NHC

3

H

6

(n)

6.44

—NHCH(CH

3

)

3

6.45

—NH

2

Melting point 159-160° C.

6.46

C

6

F

5

O—

—NH

2

Melting point 203-204° C.

6.47

—N(n-C

3

H

7

)

2

—NH

2

6.48

—N(n-C

3

H

7

)

2

—NH

2

Melting point 184-185° C.

6.49

C

6

F

5

O—

—NH

2

Melting point 134-135° C.

6.50

—N(CH

3

)

2

—NH

2

6.51

—N(CH

3

)

2

—N(CH

3

)

2

6.52

—N(C

2

H

5

)

2

—NH

2

6.53

C

6

F

5

O—

—NH

2

Melting point 104-105° C.

6.54

—NHCH

2

CH

2

CH

3

—NHCH

2

CH

2

CH

3

Melting point 104-106° C.

6.55

C

6

F

5

O—

—NH

2

Melting point 184-185° C.

6.56

C

6

F

5

O—

—NH

2

Melting point 163-164° C.

6.57

—NH

2

Melting point 193-194° C.

6.58

—NH

2

6.59

—N(C

2

H

5

)

2

—NH

2

6.60

—NH

2

13

C-NMR: 166.0 ppm; 164.6 ppm, 159.7 + 156.5 ppm, 153.0 + 149.7 ppm, 105-117 ppm

6.61

C

6

F

5

O—

—NH

2

6.62

—N(CH

3

)

2

—N(CH

3

)

2

6.63

C

6

F

5

O—

—NH

2

Melting point 181-182° C. (Decom- position)

6.64

—N(CH

3

)

2

—N(C

2

H

5

)

2

6.65

—NHCH

3

—NHCH

3

6.66

—N(C

2

H

5

)

2

—N(C

2

H

5

)

2

6.67

—NH

2

Melting point 208-209° C.

6.68

—NH

2

6.69

—NH

2

6.70

—N(CH

3

)

2

—NHCH(CH

3

)

2

6.71

—N(CH

3

)

2

—NH

2

6.72

—NH(CH

2

)

3

CF

3

—NH

2

Melting point 80-81° C.

6.73

C

6

F

5

O—

—NH

2

Melting point 175-176° C.

6.74

—NH

2

Melting point 147-148° C.

6.75

C

6

F

5

O—

—NH

2

MS: [M

+

+ H, 35%] 492, [M

+

, 40%] 491

6.76

—NH

2

6.77

C

6

F

5

O—

—NH

2

Melting point 198-199° C. (Decom- position)

6.78

—N(CH

3

)

2

—NHC

3

H

7

(n)

6.79

—NH

2

6.80

—N(CH

3

)

2

—NHC

2

H

5

6.81

—NH

2

Melting point >220° C.

6.82

—NH

2

6.83

—NH

2

Melting point 133-134° C.

6.84

C

6

F

5

O—

—NH

2

13

C-NMR: 165.4 ppm; 164.5 ppm; 53.7 ppm; 53.4 ppm; 33.3 ppm; 27.3 ppm; 25.9 ppm; 25.4 ppm; 25.3 ppm; 24.3 ppm; 24.2 ppm

6.85

—NH

2

Melting point 144-145°°C.

6.86

C

6

F

5

O—

—NHhd 2

6.87

—NH

2

6.88

—N(CH

3

)

2

—NHCH

3

6.89

—NH

2

Melting point 187-188° C.

6.90

C

6

F

5

O—

—NH

2

Melting point 187-188° C. (Decom- position)

6.91

—N(CH

3

)

2

6.92

C

6

F

5

O—

—NH

2

13

C-NMR: 164.9 ppm; 165.2 ppm; 21.1-53.7 ppm

6.93

C

6

F

5

O—

—NH

2

13

C-NMR: 165.7 ppm; 164.7 ppm; 21.2-53.6 ppm

6.94

C

6

F

5

O—

—NH

2

6.95

—NH

2

6.96

—N(CH

3

)

2

—NH

2

6.97

—N(C

4

H

9

(n))

2

—NH

2

6.98

C

6

F

5

O—

—NH

2

6.99

C

6

F

5

S—

—NH

2

Melting point 191° C. (Decom- position)

6.100

—NH

2

6.101

C

6

F

5

O—

—NH

2

6.102

C

6

F

5

O—

—NH

2

MS: [M

+

+ H] 464

6.103

—NH

2

6.104

—NH

2

6.105

—NH

2

Melting point 165-166° C.

6.106

C

6

F

5

O—

—NH

2

6.107

—NH

2

Melting point 191-192° C.

6.108

—N(C

2

H

5

)

2

—NH

2

6.109

—N(CH

3

)

2

—NH

2

Melting point 166-167° C.

6.110

—N(CH

3

)

2

—NH

2

6.111

—NH

2

6.112

—N(CH

3

)

2

—NH

2

6.113

C

6

F

5

O—

—NH

2

Melting point 174-175° C.

6.114

C

6

F

5

O—

—NH

2

6.115

C

6

F

5

O—

—NH

2

MS: [M

+

+ H] 489

6.116

—NH

2

Melting point 171-172° C.

6.117

C

6

F

5

O—

—NH

2

6.118

C

6

F

5

O—

—NH

2

6.119

—NH

2

13

C-NMR: 162.9 ppm; 161.8 ppm; 62.5 ppm; 42.8 ppm; 28.8 ppm 28.3 ppm; 27.9 ppm; 27.2 ppm

6.120

—NH

2

Melting point 173-174° C.;

13

C-NMR: 165.8 ppm; 164.6 ppm, 58.6 ppm; 37.6 ppm; 27.8 ppm; 27.6 ppm; 25.9 ppm; 22.1 ppm, 21.1 ppm

6.121

—NH

2

Melting point 174-175° C.

6.122

C

6

F

5

O—

—NH

2

6.123

C

6

F

5

O—

—NH

2

6.124

C

6

F

5

O—

—NH

2

Melting point 161-162° C.

6.125

—N(CH

3

)

2

—N(CH

3

)

2

6.126

—N(CH

3

)

2

—NH

2

6.127

—NH

2

1

H-NMR: 6.8- 7.1 ppm (3H); 5.2 ppm (2H); 3.2-3.5 ppm (6H); 2.6-3.1 ppm (3H); 1.5-1.9 ppm (4H); 1.1-1.3 ppm (6H)

6.128

C

6

F

5

O—

—NH

2

6.129

—NH

2

Melting point 201-202° C. (Decom- position)

6.130

C

6

F

5

O—

—NH

2

6.131

C

6

F

5

O—

—NH

2

6.132

—NH

2

6.133

—N(CH

3

)

2

—NH

2

6.134

C

6

F

5

O—

—NH

2

6.135

—NH

2

Melting point 195-196° C.

6.136

C

6

F

5

O—

—NH

2

6.137

—NH

2

Melting point 151-152° C.

6.138

C

6

F

5

O—

—NH

2

6.139

—NH

2

Melting point 109-110° C.

6.140

C

6

F

5

O—

—NH

2

Melting point 140-141° C.

6.141

—NH

2

6.142

—N(CH

3

)

2

—NHCH

3

6.143

—NH

2

Melting point 146-147° C.

6.144

C

6

F

5

O—

—NH

2

6.145

—NH—

Melting point 135-136° C.

6.146

—N(CH

3

)

2

—N(CH

3

)

2

6.147

—NH

2

6.148

—NH

2

6.149

—NH

2

Melting point 167-168° C.

6.150

—NH

2

6.151

—NH

2

6.152

C

6

F

5

O—

—NH

2

6.153

C

6

F

5

O—

—NH

2

Melting point 161-162° C.

6.154

C

6

F

5

O—

—NH

2

Melting point 166-167° C.

6.155

—N(C

4

H

9

(n))

2

—N(CH

3

)

2

6.156

—NH

2

6.157

—NH

2

6.158

C

6

F

5

O—

—NH

2

6.159

—NH

2

Melting point 195-196° C.

6.160

—N(CH

3

)

2

—N(CH

3

)

2

6.161

—NH

2

6.162

—N(CH

3

)

2

—NHC

4

H

9

(n)

6.163

—N(CH

3

)

2

—NHCH

3

6.164

—NH

2

Melting point 196-197° C. (Decom- position)

6.165

C

6

F

5

O—

—NH

2

Resin; 2 diastereomers:

13

C-NMR: 164.3-164.8 ppm (4 signals)

6.166

—NH

2

6.167

—NH

2

6.168

C

6

F

5

O—

—NH

2

Melting point 128-129° C.

6.169

C

6

F

5

O—

—NH

2

6.170

C

6

F

5

O—

—NH

2

Melting point 145-146° C.

6.171

—N(CH

3

)

2

—N(CH

3

)

2

6.172

—N(C

2

H

5

)

2

—NH

2

6.173

—NH

2

Melting point 139-140° C.

6.174

—NH

2

Melting point 192-193° C.

6.175

—N(CH

3

)

2

—N(C

2

H

5

)

2

6.176

—N(CH

3

)

2

—NH

2

6.177

C

6

F

5

O—

—NH

2

Melting point 124-125° C.

6.178

—NH

2

6.179

—N(CH

3

)

2

—NH

2

6.180

—NH

2

6.181

C

6

F

5

O—

—NH

2

Melting point 180-181° C.

6.182

—N(CH

3

)

2

—NH

2

6.183

—NHC

3

H

7

(n)

—NH

2

6.184

—N(CH

3

)

2

—NH

2

6.185

C

6

F

5

O—

—NH

2

Melting point 173-174° C.

6.186

—N(C

2

H

5

)

2

—NH

2

6.187

—NH

2

6.188

—N(CH

3

)

2

—N(CH

3

)

2

6.189

—N(C

2

H

5

)

2

—NH

2

6.190

—NH

2

6.191

—N(CH

3

)

2

—NH

2

6.192

C

6

F

5

O—

—NH

2

Melting point 171-172° C.

6.193

—NH

2

6.194

C

6

F

5

O—

—NH

2

Melting point 168-169° C.

6.195

—N(Ch

3

)

2

—NH

2

6.196

—N(CH

3

)

2

—NH

2

6.197

—NH

2

6.198

C

6

F

5

O—

—NH

2

6.199

—N(C

4

H

9

(n))

2

—N(CH

3

)

2

6.200

C

6

F

5

O—

—NH

2

Melting point 160-161° C. (Decom- position)

6.201

—NH

2

6.202

—N(CH

3

)

2

—N(C

2

H

5

)

2

6.203

—NH—C

4

H

9

(n)

—NH

2

6.204

—N(CH

3

)

2

—NH

2

6.205

—NH

2

Melting point 160-161° C.

6.206

—N(CH

3

)

2

—NH

2

6.207

—N(CH

3

)

2

—NH

2

6.208

—N(C

2

H

5

)

2

—NH

2

6.209

—NH

2

6.210

C

6

F

5

O—

—NH

2

6.211

—NH

2

6.212

—N(C

2

H

5

)

2

—N(C

2

H

5

)

2

6.213

—N(C

2

H

5

)

2

—NHCH

3

6.214

—N(CH

3

)

2

—NH

2

6.215

C

6

F

5

O—

—NH

2

Melting point 88-89° C.

6.216

—NH

2

Melting point 179-180° C.

6.217

—NH

2

6.218

—N(C

2

H

5

)

2

—N(CH

3

)

2

6.219

—N(CH

3

)

2

—NHC

3

H

7

(n)

6.220

—NHCH

3

—NHCH

3

6.221

—NH

2

Melting point 169-170° C. (Decom- position)

6.222

C

6

F

5

O—

—NH

2

6.223

—NH

2

Melting point 168-169° C.

6.224

(CH

3

)

2

N—

—NH

2

6.225

—N(C

2

H

5

)

2

6.226

—N(C

2

H

5

)

2

—NHCH

3

6.227

—N(CH

3

)

2

—N(CH

3

)

2

6.228

—N(C

4

H

9

(n))

2

—NH

2

6.229

C

6

F

5

O—

—NH

2

Melting point 154-155° C. (Decom- position)

6.230

—NH

2

Melting point 199-200° C.

6.231

—NH

2

Melting point 181-182° C.

6.232

—NH

2

6.233

C

6

F

5

O—

—NH

2

6.234

—NH

2

Melting point 160-161° C.

6.235

—NH

2

6.236

(CH

3

)

2

N—

—NH

2

6.237

—NH

2

Melting point 176-177° C.

6.238

—N(CH

3

)

2

6.239

—NH

2

Melting point 188-189° C.

6.240

—N(CH

3

)

2

—N(C

2

H

5

)

2

6.241

—N(CH

3

)

2

—NH

2

6.242

—NH

2

Melting point 185-186° C.

6.243

—N(CH

3

)

2

—NH

2

6.244

—N(C

2

H

5

)

2

—NHCH

3

6.245

—NH

2

6.246

C

6

F

5

O—

—NH

2

6.247

—N[CH(CH

3

)

2

]

2

C

6

F

5

O—

—NH

2

Melting point

153-154° C.

6.248

—N(CH

3

)

2

—NH

2

6.249

—NH

2

Melting point 175-176° C.

6.250

—N(CH

3

)

2

—N(CH

3

)

2

6.251

—N(C

2

H

5

)

2

—NH

2

6.252

—NHCH

3

6.253

C

6

F

5

O—

—NH

2

6.254

—NH

2

Melting point 106-107° C.

6.255

—N(CH

3

)

2

—NH

2

6.256

—NH

2

6.257

C

6

F

5

O—

—NH

2

Melting point 160-161° C.

6.258

—N(C

2

H

5

)

2

—NHCH

3

6.259

—N(CH

3

)

2

—N(CH

3

)

2

6.260

—NH

2

1

H-NMR: 6.8- 7.1 ppm (3H); 5.4 ppm (2H); 3.0-3.4 ppm (2H); 2.7 ppm (1H)

6.261

C

6

F

5

O—

—NH

2

6.262

—N(CH

3

)

2

—NH

2

6.263

—N(CH

3

)

2

—NH

2

6.264

—NH

2

6.265

—NH

2

Melting point 172-173° C. (Decom- position)

6.266

—N(CH

3

)

2

—NH

2

6.267

—N(CH

3

)

2

—N(C

3

H

7

(n))

2

6.268

—N(CH

3

)

2

—NH

2

6.269

C

6

F

5

O—

—NH

2

Melting point 145-146° C. (Decom- position)

6.270

—NH

2

6.271

—N(CH

3

)

2

6.272

—N(CH

3

)

2

—NHC

4

H

9

(n)

6.273

—N(CH

3

)

2

—NH

2

6.274

C

6

F

5

O—

—NH

2

6.275

—NH

2

Melting point 153-154° C.

6.276

—NH

2

6.277

—N(CH

3

)

2

—NH

2

6.278

—NH

2

Melting point 101-103° C.

6.279

—N(C

2

H

5

)

2

—N(C

2

H

5

)

2

6.280

—NH

2

6.281

C

6

F

5

O—

—NH

2

MS: [M

+

, 50%] 561, [M

+

+ H, 30%] 562

6.282

C

6

F

5

O—

—NH

2

Melting point 157-158° C.

6.283

C

6

F

5

O—

—NH

2

Melting point 133-134° C.

6.284

C

6

F

5

O—

—NH

2

6.285

C

6

F

5

O—

—NH

2

Melting point 137-138° C.

6.286

C

6

F

5

O—

—NH

2

MS: [M

+

, 50%] 449, [M

+

+ H, 40%] 450

6.287

C

6

F

5

O—

—NH

2

Melting point 129-130° C.

6.288

C

6

F

5

O—

—NH

2

MS: [M

+

, 40%] 449, [M

+

+ H, 40%] 450

6.289

C

6

F

5

O—

—NH

2

Melting point 157-158° C. (Decom- position)

6.290

C

6

F

5

O—

—NH

2

Melting point 112-113° C.

6.291

C

6

F

5

O—

—NH

2

Melting point 154-155° C.

6.292

C

6

F

5

O—

—NH

2

Melting point 165-166° C.

6.293

C

6

F

5

O—

—NH

2

13

C-NMR (ppm): 165.8; 164.5; 62.2; 47.7; 41.9; 31.9; 30.7; 29.5; 24.9; 24.8; 19.2

6.294

C

6

F

5

O—

—NH

2

Melting point 181-182° C.

6.295

C

6

F

5

O—

—NH

2

Melting point 162-163° C.

6.296

C

6

F

5

O—

—NH

2

Melting point 147-148° C.

6.297

C

6

F

5

O—

—NH

2

Melting point 134-135° C.

6.298

C

6

F

5

O—

—NH

2

Melting point 158-159° C.

6.299

C

6

F

5

O—

—NH

2

Resin

6.300

C

6

F

5

O—

—NH

2

Melting point 165-166° C.

6.301

C

6

F

5

O—

—NH

2

Melting point 177-178° C. (Decom- position)

6.302

—NH

2

Melting point 174-175° C.

6.303

—N(CH

3

)

2

Melting point 125-126° C.

6.304

—OH

—NH

2

Melting point 207-208-C.

6.305

—OH

—NH

2

Melting point 178-180° C.

6.306

—OH

—NH

2

Melting point 176-177° C.

6.307

—OH

—NH

2

Melting point 170-171° C.

6.308

—OH

—NH

2

Melting point 203-204° C.

6.309

—OH

—NH

2

Melting point 187-188° C.

6.310

—N(CH

3

)

2

Resin; analysis: C

19

H

29

N

5

S calc. found [%] [%] N 17.88 17.86 S 16.38 16.36

6.311

C

6

F

5

O—

—NH

2

6.312

C

6

F

5

O—

—NH

2

Melting point 150-151° C.

6.313

C

6

F

5

O—

—NH

2

Melting point 191-192° C.

6.314

C

6

F

5

O—

—NH

2

6.315

C

6

F

5

O—

—NH

2

6.316

C

6

F

5

O—

—NH

2

6.317

C

6

F

5

O−

—NH

2

6.318

C

6

F

5

O—

—NH

2

6.319

C

6

F

5

O—

—NH

2

6.320

—NH

2

Melting point 168-169° C.

6.321

—NH

2

Melting point 174-175° C. (Decom- position)

6.322

C

6

F

5

O—

—NH

2

Melting point 171-172° C.

6.323

C

6

F

5

O—

—NH

2

6.324

C

6

F

5

O—

—NH

2

Melting point 138-139° C.

6.325

C

6

F

5

O—

—NH

2

Melting point 134-135° C.

6.326

C

6

F

5

O—

—NH

2

Melting point 122-123° C.

6.327

C

6

F

5

O—

—NH

2

6.328

C

6

F

5

O—

—NH

2

6.329

C

6

F

5

O—

—NH

2

6.330

C

6

F

5

O—

—NH

2

6.331

—NH

2

Melting point 179-180° C.

6.332

C

6

F

5

O—

—NH

2

Melting point 166-167° C.

6.333

C

6

F

5

O—

—NH

2

Melting point 173-174° C.

6.334

—NH-Adamant-1-yl

C

6

F

5

O—

—NH

2

6.335

—NH-Adamant-2-yl

C

6

F

5

O—

—NH

2

Example H20

Preparation of 3-amino-5-chloro-1-(3-hexyloxy)thiatriazine

13.6 g of a 22% methylmagnesium chloride solution in THF (0.040 mol) are added to a solution of 4.1 g of 3-hexanol (0.040 mol) in 40 ml of absolute tetrahydrofuran (THF) at a temperature of −70° to −60° C., under a nitrogen atmosphere and with vigorous stirring. After thawing to 20° C., the solution is added dropwise to a solution, cooled to −65° C., of 8.2 g of 1,3,5-trichlorothiatriazine (0.040 mol) in 50 ml of absolute THF, while stirring vigorously. After warming to 0° C., the resulting colourless solution is treated with ammonia, while stirring vigorously. After the intermediate (3,5-dichloro-1-(3-hexyloxy)thiatriazine) has reacted further, 1 l of water is added to the reaction mixture. The resulting suspension is filtered with suction and the residue is rinsed with water and dissolved in methylene chloride, and the solution is dried over sodium sulfate. After the solvent has been evaporated off, the residue is stirred with pentane and the desired product is isolated as white crystals of melting point 144° C. by filtration with suction.

The compounds listed in the following Table 7 can be prepared analogously to Example H20.

TABLE 7

Compounds of the formula VIII

(VIII)

Comp.

No.

Process

R

7

R

2

Physical data

7.1

—CH

2

CH

2

Cl

—NH

2

7.2

—CH

2

CH

2

C

6

H

5

—N(CH

3

)C

4

H

9

(n)

7.3

—CH(CH

3

)

2

—NH

2

7.4

—CH

2

CH

2

Cl

—N(CH

3

)

2

7.5

—NH

2

7.6

—NH

2

7.7

—NH

2

7.8

—CH

2

CH

2

C

6

H

5

7.9

—NH

2

7.10

—NH

2

7.11

—CH

2

CH

2

Cl

—NHC(CH

3

)

3

7.12

—NH

2

7.13

—CH

2

CH

2

Cl

7.14

—NH

2

7.15

—NH

2

7.16

—NH

2

7.17

—NH

2

7.18

—NH

2

7.19

—NH

2

7.20

—CH

2

CH

2

Cl

7.21

—NH

2

7.22

—NH

2

7.23

—CH

2

CH═CH

2

—NH

2

7.24

—NH

2

7.25

7.26

—(CH

2

)

6

CH

3

—NH

2

7.27

—NH

2

7.28

—NH

2

7.29

—NH

2

7.30

—CH

2

CH

2

NO

2

—NH

2

7.31

—CH

2

C

6

F

5

—NH

2

7.32

—NH

2

7.33

—NH

2

7.34

—CH

3

—NHCH

2

CH

2

CH

3

7.35

—NH

2

7.36

—NH

2

7.37

—CH

2

CH

2

Cl

7.38

—NH

2

7.39

—CH

3

—N(CH

3

)

2

7.40

—NH

2

7.41

—NH

2

7.42

—NH

2

7.43

—NH

2

7.44

—NH

2

7.45

—CH

2

CH

2

Cl

—NHCH

2

CH

2

CH

3

7.46

—NH

2

7.47

—NH

2

7.48

—NH

2

7.49

—NH

2

7.50

—CH

2

CH

2

COOC

2

H

5

—NH

2

7.51

—NH

2

7.52

—CH

2

C≡CH

—NH

2

7.53

—NH

2

7.54

—NH

2

7.55

—CH

3

—NH

2

7.56

—NH

2

7.57

—NH

2

7.58

—NHCH

3

7.59

—NH

2

7.60

—NH

2

7.61

—CH

2

CH

2

CCl

3

—NH

2

7.62

—NH

2

7.63

—NH

2

7.64

—NH

2

7.65

—NH

2

7.66

—NH

2

7.67

—CH

2

-adamantyl

—NH

2

7.68

—NH

2

7.69

—NH

2

7.70

—NH

2

7.71

—NH

2

7.72

—NH

2

7.73

—NH

2

7.74

7.75

—NH

2

7.76

—CH

2

CH

2

OCH

3

—NH

2

7.77

—NHC

4

H

9

(n)

7.78

—NH

2

7.79

—NH

2

7.80

—NH

2

7.81

—NH

2

7.82

—CH

2

CH

2

F

—NH

2

7.83

—NH

2

7.84

—(CH

2

)

7

CH

3

—NHCH

3

7.85

—NH

2

7.86

—C

2

H

5

—NH

2

7.87

—CH(CH

3

)C

2

H

5

—NH

2

7.88

—C(CH

3

)

3

—NH

2

7.89

—NH

2

7.90

—NH

2

7.91

—CH

3

—NHC(CH

3

)

3

7.92

—NH

2

7.93

—NH

2

7.94

—NH

2

7.95

—NH

2

7.96

—NH

2

7.97

—NHCH(CH

3

)CH

2

OCH

3

7.98

—NH

2

7.99

—NH

2

7.100

—NH

2

7.101

—C

2

H

5

—NH

2

7.102

—NH

2

7.103

—NH

2

7.104

—NH

2

7.105

—NH

2

7.106

—NH

2

7.107

—NH

2

7.108

—NH

2

7.109

—NHCH

3

7.110

—NH

2

7.111

—NH

2

7.112

—NH

2

7.113

—NH

2

7.114

—NH

2

7.115

—NH

2

7.116

—NH

2

7.117

—NH

2

7.118

—NH

2

7.119

—NHC

2

H

5

7.120

—NH

2

7.121

—NH

2

7.122

—NH

2

7.123

—(CH

2

)

4

CH

3

—NH

2

7.124

—NH

2

7.125

—CH

2

CH

2

SC

2

H

5

—NH

2

7.126

—CH

2

CH

2

Si(CH

3

)

3

—NH

2

7.127

—(CH

2

)

9

CH

3

—NH

2

7.128

—NH

2

7.129

—NH

2

7.130

—NH

2

7.131

—NH

2

7.132

—(CH

2

)

2

(CF

2

)

3

CF

3

—NH

2

7.133

—NH

2

7.134

—CH

2

CH(C

6

H

5

)

2

—NH

2

7.135

—NH

2

7.136

—NH

2

7.137

—NH

2

7.138

—CH

2

CH

2

Cl

—NHCH

2

CH

2

CH

3

7.139

—NHC

4

H

9

(n)

7.140

—NH

2

7.141

—NH

2

7.142

—CH

2

CH

2

Cl

—NHCH(CH

3

)

2

7.143

—CH

2

CH

2

Cl

—N(C

2

H

5

)

2

7.144

—NH

2

7.145

—NH

2

7.146

—NH

2

7.147

—CH

2

CH

2

Cl

7.148

—NH

2

7.149

—NH

2

7.150

—NH

2

7.151

—NH

2

7.152

—NH

2

7.153

—NH

2

7.154

—NH

2

7.155

—NH

2

7.156

—NH

2

7.157

—NH

2

7.158

—NH

2

7.159

—NH

2

7.160

—NH

2

7.161

—NH

2

7.162

—NH

2

7.163

—NH

2

7.164

—NH

2

7.165

—NH

2

7.166

—NH

2

7.167

—NH

2

7.168

—NH

2

7.169

—NH

2

7.170

—NH

2

7.171

—NH

2

7.172

—NH

2

7.173

—NH

2

7.174

—NH

2

7.175

—NH

2

7.176

—NH

2

7.177

—NH

2

7.178

—NH

2

7.179

—NH

2

7.180

—NH

2

7.181

—NH

2

7.182

—NH

2

7.183

—NH

2

7.184

—NH

2

7.185

—NH

2

7.186

—NH

2

7.187

—NH

2

7.188

—(CH

2

)

3

Si(CH

3

)

3

—NH

2

7.189

—NH

2

7.190

b

4

—NH

2

Melting point 144° C. (Decomposition)

7.191

—NH

2

7.192

—NH

2

7.193

—CH

2

Si(CH

3

)

3

—NH

2

7.194

—NHC

2

H

5

7.195

—NHCH

3

7.196

—NH

2

7.197

—NH

2

7.198

—NH

2

7.199

—NH

2

7.200

—NH

2

7.201

—CH(CH

3

)—Si(CH

3

)

3

—NH

2

7.202

—CH(CH

3

)COOCH

3

—NH

2

7.203

b

4

—NH

2

Melting point 144° C.

7.204

—NH

2

7.205

b

4

—CH[CH

2

CH(CH

3

)

2

]

2

—NH

2

1

H-NMR (CDCl

3

, ppm): 6.3 (broad s, 1H); 5,4 (broad s, 1H); 4.25-4.35 (m, 1H); 1.9-1.3(m, 6H); 1.0-0.83(m, 12H)

7.206

—NH

2

7.207

—NH

2

7.208

—NH

2

7.209

—NH

2

7.210

—NH

2

7.211

—NH

2

7.212

—NH

2

7.213

—NH

2

7.214

—NH

2

7.215

—NH

2

7.216

—NH

2

7.217

—NH

2

7.218

—NH

2

7.219

—NH

2

7.220

—NH

2

7.221

—NH

2

7.222

—NH

2

7.223

—NH

2

7.224

—NH

2

7.225

—NH

2

7.226

—NH

2

7.227

—NH

2

7.228

—NH

2

7.229

—NH

2

7.230

—NH

2

7.231

—CH

2

CH

2

C

6

F

5

—NH

2

7.232

—NH

2

7.233

—NH

2

7.234

—NH

2

7.235

—NH

2

Example H21

Preparation of 3,5-dichloro-1-(octahydroindol-1-yl)thiatriazine

A mixture of 3.1 g of octahydroindol (0.025 mol) and 2.5 g of triethylamine (0.025 mol) is added dropwise to a solution of 5.1 g of 1,3,5-trichlorothiatriazine (0.025 mol) in 65 ml of diethyl ether at a temperature of −70° to −60° C., under a nitrogen atmosphere and with vigorous stirring. After the reaction mixture has thawed, water is added and the organic phase is washed with water, sodium bicarbonate solution and brine, dried over sodium sulfate and evaporated. After crystallization from pentane, crystals of the desired compound of melting point 90-92° C. are isolated.

The compounds listed in the following Table 8 can be prepared analogously to Example H21.

TABLE 8

Compounds of the the formula IX

(IX)

Comp.

No.

R

1

Physical data

8.1

—NHCH

2

CH

2

CH

3

8.2

8.3

8.4

8.5

8.6

8.7

8.8

8.9

8.10

8.11

8.12

8.13

8.14

8.15

—N(CH

2

CH

2

CN)

2

8.16

—NHC

6

H

11

(c)

8.17

—N(n-C

3

H

7

)

2

8.18

8.19

8.20

8.21

8.22

8.23

8.24

8.25

8.26

8.27

8.28

8.29

8.30

8.31

—N[CH(CH

3

)

2

]

2

8.32

—(C

2

H

5

)

2

8.33

—N(C

2

H

5

)C

4

H

9

(n)

8.34

8.35

8.36

8.37

—N(CH

3

)

2

8.38

8.39

8.40

8.41

8.42

—N(C

2

H

5

)

2

8.43

(not isolated)

8.44

8.45

8.46

8.47

8.48

8.49

8.50

—NHCH

3

8.51

8.52

8.53

—NH(CH

2

)

3

CF

3

8.54

8.55

8.56

8.57

8.58

8.59

8.60

8.61

8.62

8.63

8.64

8.65

8.66

8.67

8.68

8.69

—N(C

4

H

9

(n))

2

8.70

8.71

8.72

8.73

8.74

8.75

8.76

8.77

8.78

8.79

8.80

Melting point 90-92° C.

8.81

8.82

8.83

—N(CH

3

)

2

8.84

8.85

8.86

8.87

8.88

8.89

8.90

8.91

8.92

8.93

8.94

8.95

8.96

8.97

8.98

8.99

8.100

8.101

8.102

8.103

—N(C

4

H

9

(n))

2

8.104

8.105

8.106

8.107

8.108

8.109

8.110

8.111

8.112

8.113

8.114

8.115

—NHC

3

H

7

(n)

8.116

8.117

8.118

8.119

8.120

8.121

8.122

8.123

—NH—C

4

H

9

(n)

8.124

8.125

8.126

8.127

8.128

8.129

8.130

8.131

8.132

8.133

8.134

8.135

8.136

8.137

8.138

8.139

—N[CH(CH

3

)

2

]

2

8.140

8.141

8.143

8.144

8.145

8.146

8.147

8.148

8.149

8.150

8.151

8.152

8.153

8.154

8.155

8.156

8.157

8.158

(not isolated)

8.159

8.160

8.161

8.162

8.163

8.164

8.165

8.166

8.167

8.168

8.169

8.170

8.171

8.172

8.173

8.174

8.175

8.176

8.177

8.178

8.179

8.180

8.181

8.182

8.183

8.184

8.185

8.186

8.187

8.188

Example H22

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

15.6 ml of a 1.6 molar n-butyllithium solution in hexane (0.025 mol) are added to a solution of 2.13 g of piperidine (0.025 mol) in 10 ml of absolute tetrahydrofuran at a temperature of −70° to −60° C., under a nitrogen atmosphere and with vigorous stirring. After thawing to 20° C., the resulting white suspension is added dropwise in portions to a solution, cooled to −60° C., of 5.11 g of 1,3,5-trichlorothiatriazine (0.025 mol) in 50 ml of absolute tetrahydrofuran, while stirring vigorously. After warming to −10° C. the reaction mixture is treated with ammonia (gas) with vigorous stirring. After all the intermediate has been used up, water and ethyl acetate are added to the reaction mixture. The organic phase is washed with water and brine, dried over sodium sulfate and evaporated. The residue is stirred with a diethyl ether/pentane mixture and filtered off with suction. The desired compound is isolated as yellowish crystals of melting point 118-120° C. (decomposition).

Example H23

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

10.2 g of a 30% ammonia solution in water (0.180 mol) are added to a solution of 3.7 g of 3,5dichloro-1-(octahydroindol-1-yl)thiatriazine (0.0126 mol) in 120 ml of tetrahydrofuran at 20° C. and the mixture is stirred vigorously for 3 hours. After evaporation of the organic solvent, the resulting suspension is filtered off with suction and the residue is washed with water and then with diethyl ether and dried. The desired compound is isolated as slightly yellowish crystals of melting point 115° C. (decomposition).

The compounds listed in the following Table 9 can be prepared analogously to Examples H22 and H23.

TABLE 9

Compounds of the formula X

(X)

Comp.

No.

R

1

R

2

Physical data

9.1

—NHCH

2

CH

2

CH

3

—NH

2

9.2

—N(CH

3

)

2

9.3

—NH

2

9.4

—NH

2

9.5

—NH

2

9.6

—NH

2

9.7

—NH

2

9.8

—NH

2

9.9

—NH

2

9.10

—NH

2

9.11

—NH

2

9.12

—NH

2

9.13

—NH

2

9.14

—NH

2

9.15

—NH

2

9.16

—N(CH

2

CH

2

CN)

2

—NH

2

9.17

—NHC

6

H

11

(c)

—NH

2

9.18

—NH

2

9.19

—N(n-C

3

H

7

)

2

—NH

2

9.20

—NH

2

9.21

—NH

2

9.22

—NH

2

9.23

—NH

2

9.24

—NH

2

9.25

—NH

2

9.26

—NH

2

9.27

—NH

2

9.28

—NH

2

9.29

—NH

2

9.30

—NH

2

9.31

—NH

2

9.32

—NH

2

9.33

—N[CH(CH

3

)

2

]

2

—NH

2

9.34

—N(C

2

H

5

)C

4

H

9

(n)

—NHCH

3

9.35

—NH

2

9.36

—NH

2

9.37

—NH

2

9.38

—NHCH(CH

3

)

3

9.39

—NH

2

9.40

—NH

2

9.41

—N(n-C

3

H

7

)

2

—NH

2

9.42

—NH

2

9.43

—N(CH

3

)

2

—NH

2

9.44

—N(CH

3

)

2

—N(CH

3

)

2

9.45

—N(C

2

H

5

)

2

—NH

2

9.46

—NH

2

Melting point 118-120° C. (Decomposition)

9.47

—NHCH

2

CH

2

CH

3

—NHCH

2

CH

2

CH

3

9.48

—NH

2

9.49

—NH

2

9.50

—NH

2

9.51

—NH

2

9.52

—NH

2

9.53

—NH

2

9.54

—NH

2

9.55

—N(CH

3

)

2

—N(C

2

H

5

)

2

9.56

—NHCH

3

—NHCH

3

9.57

—N(C

2

H

5

)

2

—N(C

2

H

5

)

2

9.58

—NH

2

9.59

—NH

2

9.60

—N(CH

3

)

2

—NHCH(CH

3

)

2

9.61

—NH(CH

2

)

3

CF

3

—NH

2

9.62

—NH

2

9.63

—NH

2

9.64

—NH

2

9.65

—NH

2

9.66

—NH

2

9.67

—N(CH

3

)

2

—NHC

3

H

7

(n)

9.68

—NH

2

9.69

—N(CH

3

)

2

—NHC

2

H

5

9.70

—NH

2

9.71

—NH

2

9.72

—NH

2

9.73

—NH

2

9.74

—NH

2

9.75

—N(CH

3

)

2

—NHCH

3

9.76

—N(CH

3

)

2

9.77

—NH

2

9.78

—NH

2

9.79

—NH

2

9.80

—NH

2

9.81

—N(C

4

H

9

(n))

2

—NH

2

9.82

—NH

2

9.83

—NH

2

9.84

—NH

2

9.85

—NH

2

9.86

—NH

2

9.87

—NH

2

9.88

—NH

2

9.89

—NH

2

9.90

—NH

2

9.91

—NH

2

9.92

—NH

2

9.93

—NH

2

Melting point 115° C. (Decomposition)

9.94

—NHCH

3

9.95

—NH

2

9.96

—NH

2

9.97

—NH

2

9.98

—NH

2

9.99

—NH

2

9.100

—NH

2

9.101

—NH

2

9.102

—NH

2

9.103

—NH

2

9.104

—NH

2

9.105

—NH

2

9.106

—NH

2

9.107

—NH

2

9.108

—NH

2

9.109

—NH

2

9.110

—NH

2

9.111

—NH

2

9.112

—NH

2

9.113

—NH

2

9.114

—NH

2

9.115

—NH

2

9.116

—NH

2

9.117

—N(C

4

H

9

(n))

2

—N(CH

3

)

2

9.118

—NH

2

9.119

—NH

2

9.120

—NH

2

9.121

—NH

2

9.122

—N(CH

3

)

2

—NHC

4

H

9

(n)

9.123

—NH

2

9.124

—NH

2

9.125

—NH

2

9.126

—NH

2

9.127

—NH

2

9.128

—NH

2

9.129

—NH

2

9.130

—NHC

3

H

7

(n)

—NH

2

9.131

—NH

2

9.132

—NH

2

9.133

—NH

2

9.134

—NH

2

9.135

—NH

2

9.136

—NH

2

9.137

—NH

2

9.138

—NH—C

4

H

9

(n)

—NH

2

9.139

—NH

2

9.140

—N(C

2

H

5

)

2

—NHCH

3

9.141

—NH

2

9.142

—NH

2

9.143

—N(C

2

H

5

)

2

—N(CH

3

)

2

9.144

—NH

2

9.145

—NH

2

9.146

—NH

2

9.147

—N(C

2

H

5

)

2

9.148

—NH

2

9.149

—NH

2

9.150

—NH

2

9.151

—NH

2

9.152

—N(CH

3

)

2

9.153

—NH

2

9.154

—NH

2

9.155

—NH

2

9.156

—N[CH(CH

3

)

2

]

2

—NH

2

9.157

—NH

2

9.158

—NHCH

3

9.159

—NH

2

9.160

—NH

2

9.161

—NH

2

9.162

—NH

2

9.163

—N(CH

3

)

2

—N(C

3

H

7

(n))

2

9.164

—NH

2

9.165

—N(CH

3

)

2

9.166

—N(CH

3

)

2

—NHC

4

H

9

(n)

9.167

—NH

2

9.168

—NH

2

9.169

—NH

2

9.170

—NH

2

9.171

—NH

2

9.172

—NH

2

9.173

—NH

2

9.174

—NH

2

9.175

—NH

2

9.176

—NH

2

9.177

—NH

2

9.178

—NH

2

9.179

—NH

2

9.180

—NH

2

9.181

—NH

2

9.182

—NH

2

9.183

—NH

2

9.184

—NH

2

9.185

—NH

2

9.186

—NH

2

9.187

—NH

2

9.188

—NH

2

9.189

—NH

2

9.190

—NH

2

9.191

—NH

2

9.192

—NH

2

9.193

—N(CH

3

)

2

9.194

—NH

2

9.195

—NH

2

9.196

—NH

2

9.197

—NH

2

9.198

—NH

2

9.199

—NH

2

9.200

—NH

2

9.201

—NH

2

9.202

—NH

2

9.203

—NH

2

9.204

—NH

2

9.205

—NH

2

9.206

—NH

2

9.207

—NH

2

9.208

—NH

2

9.209

—NH

2

9.210

—NH

2

9.211

—NH

2

9.212

—NH

2

9.213

—NH

2

9.214

—NH

2

9.215

—NH

2

9.216

—NH

2

9.217

—NH

2

Formulation examples for active compounds of the formula I

(%=percent by weight)

F1. Emulsion concentrates

a)

b)

c)

d)

Active compound according

5%

10%

25%

50%

to Tables 4-6

Calcium dodecylbenzenesulfonate

6%

8%

6%

8%

Castor oil polyglycol ether

4%

—

4%

4%

(36 mol of EO)

Octylphenol polyglycol ether

—

4%

—

2%

(7-8 mol of EO)

Cyclohexanone

—

—

10%

20%

Aromatic hydrocarbon mixture

85%

78%

55%

16%

C

9

-C

12

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

F2. Solutions

a)

b)

c)

d)

Active compound according

5%

10%

50%

90%

to Tables 4-6

1-Methoxy-3-(3-methoxypropoxy)propane

—

20%

20%

—

Polyethylene glycol molecular weight 400

20%

10%

—

—

N-Methyl-2-pyrrolidone

—

—

30%

10%

Aromatic hydrocarbon mixture

75%

60%

—

—

C

9

-C

12

The solutions are suitable for use in the form of tiny drops.

F3. Wettable powders

a)

b)

c)

d)

Active compound according

5%

25%

50%

80%

to Tables 4-6

Sodium lignin sulfonate

4%

—

3%

—

Sodium lauryl sulfate

2%

3%

—

4%

Sodium diisobutyl-naphthaline sulfonate

—

6%

5%

6%

Octylphenol polyglycol ether

—

1%

2%

—

(7-8 Mol EO)

Highly disperse silicic acid

1%

3%

5%

10%

Kaolin

88%

62%

35%

—

The active compound is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. Wettable powders which can be diluted with water to give suspensions of any desired concentration are obtained.

F4. Coated granules

a)

b)

c)

Active compound according

0.1%

5%

15%

to Tables 4-6

Highly disperse silicic acid

0.9%

2%

2%

Inorganic carrier (ø0.1-1 mm), for example

99.0%

93%

83%

CaCO

3

or SiO

2

The active compound is dissolved in methylene chloride, the solution is sprayed onto the carrier and the solvent is then evaporated off in vacuo.

F5. Coated granules

a)

b)

c)

Active compound according

0.1%

5%

15%

to Tables 4-6

Polyethylene glycol molecular weight 200

1.0%

2%

3%

Highly disperse silicic acid

0.9%

1%

2%

Inorganic carrier (ø0.1-1 mm), for example

98.0%

92%

80%

CaCO

3

or SiO

2

The finely ground active compound is applied uniformly to the carrier, which has been moistened with polyethylene glycol, in a mixer. Dust-free coated granules are obtained in this manner.

F6. Extruded granules

a)

b)

c)

d)

Active compound according

0.1%

3%

5%

15%

to Tables 4-6

Sodium lignin sulfonate

1.5%

2%

3%

4%

Carboxymethyl cellulose

1.4%

2%

2%

2%

Kaolin

97.0%

93%

90%

79%

The active compound is mixed with the additives and the mixture is ground and moistened with water. This mixture is extruded and the extrudate is then dried in a stream of air.

F7. Dusts

a)

b)

c)

Active compound according

0.1%

1%

5%

to Tables 4-6

Talc

39.9%

49%

35%

Kaolin

60.0%

50%

60%

Ready-to-use dusts are obtained by mixing the active compound with the carriers and grinding the mixture on a suitable mill.

F8. Suspension concentrates

a)

b)

c)

d)

Active compound according

3%

10%

25%

50%

to Tables 4-6

Ethylene glycol

5%

5%

5%

5%

Nonylphenol polyglycol ether

—

1%

2%

—

(15 mol of EO)

Sodium lignin sulfonate

3%

3%

4%

5%

Carboxymethyl cellulose

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 ground active compound is mixed intimately with the additives. A suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water is thus obtained.

BIOLOGICAL EXAMPLES

Example B1

Herbicidal Action Before Emergence of the Plants (Pre-emergent Action)

Monocotyledon and dicotyledon test plants are sown in standard soil in plastic pots. Immediately after sowing, the test substances are sprayed on (500 l of water/ha) in an aqueous suspension prepared from a 25% wettable powder (Example F3, b)), corresponding to a dosage of 2000 g of active substance/ha. The test plants are then grown under optimum conditions in a greenhouse. After a test period of 3 weeks, the test is evaluated with a ratings scale of nine levels (1=complete damage, 9=no action). Ratings of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action.

Test plants: Avena, Setaria, Sinapis, Stellaria

In this test, the compounds of the formula I according to the examples in Tables 4, 5 and 6 show a potent herbicidal action.

Table B1 gives examples of the good herbicidal activity of the compounds of the formula I:

TABLE B1

Pre-emergent action

Test plants

Compound No.

Avena

Setaria

Sinapis

Stellaria

5.52

4

2

1

1

5.78

3

2

2

1

5.86

5

3

1

1

5.120

4

2

1

1

5.127

4

2

1

1

5.131

4

2

1

1

5.146

4

1

1

1

5.176

4

2

1

1

5.317

4

2

2

1

5.321

3

1

1

1

5.326

4

4

1

1

5.327

4

3

2

1

5.329

2

1

1

1

5.332

3

1

1

1

6.10

4

4

1

1

6.27

4

3

2

1

6.30

3

2

1

1

6.34

3

1

1

1

6.37

3

2

1

1

6.42

4

2

1

1

6.53

3

3

1

1

6.63

4

3

1

1

6.77

4

3

1

1

6.89

2

2

1

1

6.92

4

1

1

1

6.93

2

1

1

1

6.124

3

1

1

1

6.129

4

4

1

1

6.135

3

3

1

1

6.140

4

3

2

1

6.145

4

2

1

1

6.153

4

3

1

1

6.154

4

1

1

1

6.170

3

4

4

1

6.173

4

3

1

1

6.185

4

4

1

1

6.192

2

1

1

1

6.194

7

5

2

2

6.200

4

1

1

1

6.229

3

2

1

1

6.257

3

2

1

1

6.282

4

2

1

1

6.285

5

2

1

1

6.292

5

1

1

1

6.295

3

1

1

1

6.296

4

2

1

1

6.298

3

2

1

1

6.302

3

2

1

1

6.331

4

2

1

1

The same results are obtained when the compounds of the formula I are formulated according to Examples F1, F2 and F4 to F8.

Example B2

Post-emergent Herbicidal Action (Contact Herbicide)

Monocotyledon and dicotyledon test plants are grown in plastic pots with standard soil in a greenhouse and, in the 4- to 6-leaf stage, are sprayed with an aqueous suspension of the test substances of the formula 1, prepared from a 25% wettable power (Example F3, b)), corresponding to a dosage of 2000 g of active substance/ha (500 l of water/ha). The test plants are then grown further in the greenhouse under optimum conditions. After a test period of about 18 days, the test is evaluated with a ratings scale of 9 levels (1=complete damage, 9=no action). Ratings of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action.

Test plants: Sinapis, Stellaria

In this test also, the compounds of the formula I according to the examples in Tables 4, 5 and 6 show a good herbicidal action.

Table B2 gives examples of the good herbicidal activity of the compounds of the formula I:

TABLE B2

Post-emergent action

Test plants

Compound No.

Sinapis

Stellaria

5.52

2

2

5.59

1

3

5.78

2

3

5.85

3

3

5.120

2

3

5.127

2

3

5.131

1

3

5.141

2

4

5.154

2

4

5.176

2

2

5.316

2

4

5.317

2

4

5.318

2

4

5.321

2

2

5.326

2

4

5.329

1

5

5.332

1

2

5.337

1

5

6.6

2

4

6.7

2

3

6.17

3

4

6.21

2

4

6.23

2

4

6.27

2

3

6.30

2

3

6.34

2

2

6.37

3

2

6.42

2

2

6.57

2

4

6.81

2

3

6.89

2

3

6.90

2

4

6.92

1

1

6.93

1

1

6.102

2

3

6.120

2

4

6.124

2

3

6.129

2

3

6.135

3

3

6.140

2

3

6.145

3

3

6.153

1

2

6.154

1

1

6.164

1

3

6.168

2

3

6.170

2

3

6.173

2

3

6.177

2

2

6.181

2

3

6.185

1

1

6.192

2

4

6.194

2

4

6.200

2

2

6.229

2

3

6.247

3

4

6.249

1

2

6.257

2

2

6.282

1

5

6.283

1

4

6.285

2

3

6.292

2

3

6.295

1

3

6.296

2

4

6.298

1

4

6.302

2

3

6.331

1

2

6.320

2

3

The same results are obtained when the compounds of the formula I are formulated according to Examples F1, F2 and F4 to F8.

Claims

1. A compound of the formula I in whichR1 is a group —OR7, —NR90R91 or in which the radicals R20 independently of one another are hydrogen, C1-C4alkyl or C1-C3alkoxy; R25 is hydrogen, chlorine, methyl or methoxy; R100 is hydrogen or C1-C3alkyl; Y1 is —O—, —S— or —NR30; R30 is hydrogen, methyl, C1-C3alkylcarbonyl or (C1-C3alkyl)2NCO; n1 is 1, 2, 3, 4 or 5; n2 is 0, 1 or 2; and n3 is a number from 3 to 10; R7 is C1-C16alkyl, C1-C16alkyl substituted by up to 9 halogens, up to 3 NO2, CN, C1-C5alkoxy, C1-C5alkylthio, C3-C8cycloalkoxy, C3-C8cycloalkylthio, C1-C3trialkylsilyl, C3-C10alkenyloxy, C3-C5alkynyloxy, C1-C5alkylcarbonyloxy, C1-C3alkoxycarbonyl, C1-C3alkylcarbonyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted up to 3 times by C1-C4alkyl, or R7 is C1-C16alkyl substituted once by C3-C8cycloalkyl, C6-C12bicycloalkyl, C6-C12chlorobicycloalkyl, C6-C12bicycloalkenyl or adamantyl, or R7 is C1-C16alkyl substituted once by up to 5 times substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring of the formula in which R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy; R100 is as defined above; R24 is hydrogen or methyl; and R101 is C1-C4alkyl, C1-C4alkylcarbonyl or C1-C3-alkoxycarbonyl, or R7 is C3-C15alkenyl, C3-C15alkenyl substituted by up to 9 halogens, up to 3 C1-C3alkoxy, C3-C8cycloalkyl, C1-C3trialkylsilyl or up to 5 times substituted or unsubstituted aryl or aryloxy, or R7 is C3-C5alkynyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted by up to 9 halogens, up to 3 CN, C1-C3trialkylsilyl, ═O, C1-C6alkyl, cyano-C1-C5alkyl, C1-C5alkyl-CONH—C1-C5alkyl, phenyl-CONH—C1-C5alkyl, C1-C5chloroalkyl, C1-C3alkoxy, C1-C3alkylthio, C1-C3alkoxycarbonyl, C1-C3alkoxycarbonyl-C1-C5alkyl, C5-C7cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, benzyl or C1-C3halogenoalkyl, or R7 is C5-C7cycloalkenyl, C5-C7cycloalkenyl substituted up to 3 times by C1-C3alkyl, or R7 is C6-C12bicycloalkyl, C6-C12bicycloalkyl substituted up to 3 times by C1-C3alkyl, cyano or halogen, C6-C12bicycloalkenyl or C6-C12bicycloalkenyl substituted up to 3 times by C1-C3alkyl, or R7 is a substituted or unsubstituted non-aromatic heterocyclic ring of the formula in which R100 and R101 are as defined above, or an alicyclic ring system; R90 and R91 independently of one another are hydrogen, C1-C12alkyl, C1-C12alkyl substituted by up to 3 halogens, NO2, CN, hydroxyl, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3trialkylsilyl, C1-C6alkylamino, di(C1-C6alkyl)amino, C3-C7cycloalkyl, or a heterocyclic ring of the formula in which R25 and R100 are as defined above, or C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl, C6-C12bicycioalkenyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted up to 4 times by C1-C4alkyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted up to 4 times by C1-C4alkyl, with the proviso that R90 and R91 are not simultaneously hydrogen; or R90 and R91, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted up to 3 times by C1-C4alkyl, C1- or C2halogenoalkyl, C1- or C2hydroxyalkyl, methoxy-C1-C4alkyl, halogen, hydroxyl, CN, C1-C4alkoxy, C1-C4alkylcarbonyl, C1- or C2halogenoalkyl, C1-C3alkoxycarbonyl, (C1-C3alkyl)2NCO, di(C1-C4alkyl)amino or ═O and can additionally be bridged by 1 or 2 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or R90 and R91, together with the nitrogen atom to which they are bonded, form a mono- or diunsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted up to 3 times or unsubstituted by C1-C4alkyl, C1- or C2halogenoalkyl, halogen, hydroxyl, CN, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, phenyl, C1-C4alkoxy or C1-C3alkoxycarbonyl and additionally bridged by 1 or 2 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused; the radicals R24 independently of one another are hydrogen or methyl; R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy; R2 is halogen, C1-C10alkoxy, C1-C10alkoxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, or R2 is C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-X—, C6-C12bicycloalkyl-X—, heterocylyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; X is —O—, —S—, —SO— or —SO2—, or R2 is a group R88R89N—, R88 and R89 independently of one another are hydrogen, C1-C6alkyl, C1-C6alkyl substituted up to 3 times by halogens, CN, C1-C3alkoxy or C3-C12cycloalkyl, C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl or C6-C12bicycloalkyl substituted up to 3 times by C1-C3alkyl; the radicals R20 independently of one another are hydrogen or C1-C4alkyl; n7 is 4 or 5; Y is —O—, —S—, —NH— or —NR101—; R98 and R101 are as defined above; R3 is halogen, hydroxyl, C1-C10alkoxy, C1-C10alkoxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, or R3 is C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-X—, C6-C12bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and X is as defined above, and stereoisomers of the compounds of the formula I, excluding the compounds of formulae I1 to I7: wherein R01 is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl; R02 is ethyl, benzyl or i-butyl and R03 is ethyl, cyclohexyl, benzyl or i-butyl, or R02 and R03, together with the nitrogen atom to which they are bonded, form a piperidine ring; R04 is chlorine, methylthio, ethylthio, i-propylthio, n-butylthio, i-butylthio, phenylthio or benzylthio; R05 is ethoxy, methylthio, ethylthio or phenylthio; and R06 is chlorine or cyclohexylamino.
2. A compound according to claim 1, in whichR1 is a group —OR7, —NR90R91 or in which the radicals R20 independently of one another are hydrogen, C1-C4alkyl or C1-C3alkoxy; R25 is hydrogen, chlorine, methyl or methoxy; R100 is hydrogen or C1-C3alkyl; Y1 is —O—, —S— or —NR30; R30 is hydrogen, methyl, C1-C3alkylcarbonyl or (C1-C3alkyl)2NCO; n1 is 1, 2, 3,4 or 5; n2 is 0, 1 or 2; and n3 is a number from 3 to 10; R7 is C1-C16alkyl, C1-C16alkyl substituted by halogen, NO2, CN, C1-C5alkoxy, C1-C5alkylthio, C3-C8cycloalkoxy, C1-C3trialkylsilyl, C3-C10alkenyloxy, C3-C5alkynyloxy, C1-C5alkyl-carbonyloxy, C1-C3alkoxycarbonyl, C1-C3alkylcarbonyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by C1-C4alkyl, or R7 is C1-C16alkyl substituted by C3-C8cycloalkyl, C6-C12bicycloalkyl, C6-C12chlorobicycloalkyl, C6-C12bicycloalkenyl or adamantyl, or R7 is C1-C16alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethylenoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring of the formula in which R24, R98, R100 and R101 are as defined in claim 1, or R7 is C3-C15alkenyl, C3-C15alkenyl substituted by halogen, C1-C3alkoxy, C3-C8cycloalkyl or substituted or unsubstituted aryl or aryloxy, or R7 is C3-C5alkynyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted by halogen, CN, C1-C3-trialkylsilyl, ═O, C1-C6alkyl, cyano-C1-C5alkyl, C1-C5alkyl-CONH—C1-C5alkyl, phenyl-CONH—C1-C5alkyl, C1-C5chloroalkyl, C1-C3alkoxy, C1-C3alkylthio, C1-C3alkoxycarbonyl, C1-C3alkoxycarbonyl-C1-C5alkyl, C5-C7cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, benzyl or C1-C3halogenoalkyl, or R7 is C5-C7cycloalkenyl, C5-C7cycloalkenyl substituted by C1-C3alkyl, or R7 is C6-C12bicycloalkyl, C6-C12bicycloalkyl substituted by C1-C3alkyl or halogen, C6-C12bicycloalkenyl, C6-C12bicycloalkenyl substituted by C1-C3alkyl, or R7 is a substituted or unsubstituted nonaromatic heterocyclic ring of the formula in which R100 and R101 are as defined above, or an alicyclic ring system; R90 and R91 independently of one another are hydrogen, C1-C12alkyl, C1-C12alkyl substituted by halogen, NO2, CN, hydroxyl, C1-C3alkoxy, C1-C3trialkylsilyl, C1-C6alkylamino, di(C1-C6alkyl)amino, C3-C7cycloalkyl, or a heterocyclic ring of the formula in which R25 and R100 are as defined above, or R90 and R91 independently of one another are C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl, C6-C12bicycloalkenyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted by C1-C4alkyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by C1-C4alkyl, with the proviso that R90 and R91 are not simultaneously hydrogen; or R90 and R91, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C1-C4alkyl, C1- or C2-halogenoalkyl, methoxy-C1-C4alkyl, halogen, hydroxyl, CN, C1-C4alkoxy, C1-C4alkylcarbonyl, C1- or C2halogenoalkyl, C1-C3alkoxycarbonyl, (C1-C3alkyl)2NCO, di(C1-C4alkyl)amino or ═O and can additionally be bridged by 1 or 2 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or R90 and R91, together with the nitrogen atom to which they are bonded, form a monounsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C1-C4alkyl, C1- or C2halogenoalkyl, halogen, hydroxyl, CN, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, phenyl, C1-C4alkoxy or C1-C3alkoxycarbonyl and is additionally bridged by 1 or 2 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused; the radicals R24 independently of one another are hydrogen or methyl; R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3-alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy; R2 is halogen, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R2 is C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8oycloalkyl-X—, C6-C12bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; X is —O—, —S—, —SO— or —SO2—, or R2 is a group R88R89N—, R88 and R89 independently of one another are hydrogen, C1-C6alkyl, C1-C6alkyl substituted by halogen, CN, C1-C3alkoxy or C3-C12cycloalkyl, C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl or C6-C12bicycloalkyl substituted by C1-C3alkyl; the radicals R20 independently of one another are hydrogen or C1-C4alkyl; n7 is 4 or 5; Y is —O—, —S—, —NH— or —NR101—; R101 is C1-C4alkyl, C1-C4alkylcarbonyl or C1-C3alkoxycarbonyl and R98 is as defined above; and R3 is halogen, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R3 is C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-X—, C6-C12bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and X is as defined above.
3. A compound according to claim 2, in which in which the radicals R20 independently of one another are hydrogen or C1-C4alkyl; R25 is hydrogen, chlorine, methyl or methoxy; R100 is hydrogen or C1-C3alkyl; Y1 is —O—, —S— or —NR30; R30 is hydrogen, methyl, C1-C3alkylcarbonyl or (C1-C3alkyl)2NCO; n1 is 1, 2, 3, 4 or 5; n2 is 0, 1 or 2; and n3 is a number from 3 to 10.
4. A compound according to claim 2, in whichR1 is the group —OR7; and R2 and R3 independently of one another are chlorine, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R2 and R3 independently of one another are C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-X—, C6-C12bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.
5. A compound according to claim 2, in whichR1 is the group —OR7; R2 is a group R88R89N—, and R3 is aryl-X—, phthalidyl-X—, biphenyl-X—, or heteroaryl-X—.
6. A compound according to claim 2, in whichR1 is a group —NR90R91 or in which the radicals R20, R25, R100, Y1, R30, n1, n2 and n3 are as defined in claim 2; R2 is a group R88R89N—, and R3 is aryl-X—, phthalidyl-X—, biphenyl-X- or heteroaryl-X—.
7. A compound according to claim 5, in whichR1 is a group —OR7; R7 C1-C16alkyl, C1-C16alkyl substituted by halogen, NO2, CN, C1-C5alkoxy, C1-C5alkylthio, C1-C8cycloalkoxy, C1-C3trialkylsilyl, C3-C10alkenyloxy, C3-C5alkynyloxy, C1-C5alkylcarbonyloxy, C1-C3alkoxycarbonyl, C1-C3alkylcarbonyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by C1-C4alkyl, or R7 is C1-C16alkyl substituted by C6-C12bicycloalkyl, C6-C12chlorobicycloalkyl, C6-C12bicycloalkenyl or adamantyl, or R7 is C1-C16alkyl substituted by in which R24 is hydrogen or methyl; R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy; R99 is hydrogen, halogen, NO2, CN, C1-C5alkyl, C1-C6alkoxy, C1-C6alkenyloxycarbonyl, C1-C3alkylthio, C1-C6alkoxycarbonyl, NH2, C1-C3alkyl-CONH, di(C1-C6alkyl)amino or C1-C6alkylamino; R100 is hydrogen or C1-C3alkyl; and R101 is C1-C4alkyl, C1-C4alkylcarbonyl or C1-C3alkoxycarbonyl; or R7 is C3-C12cycloalkyl, C3-C12cycloalkyl substituted by halogen, CN, C1-C3trialkylsilyl, ═O, C1-C6alkyl, cyano-C1-C5alkyl, C1-C5alkyl-CONH—C1-C5alkyl, phenyl-CONH—C1-C5alkyl, C1-C5chloroalkyl, C1-C3alkoxy, C1-C3alkylthio, C1-C3alkoxycarbonyl, C1-C3alkoxycarbonyl-C1-C5alkyl, C5-C7cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, benzyl or C1-C3halogenoalkyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by C1-C3alkyl, or R7 is C6-C12bicycloalkyl, C6-C12bicycloalkyl substituted by C1-C3alkyl or halogen, C6-C12bicycloalkenyl or C6-C12bicycloalkenyl substituted by C1-C3alkyl, or R7 is a substituted or unsubstituted non-aromatic heterocyclic ring of the formula in which R100 is hydrogen or C1-C3alkyl; and R101 is C1-C4alkyl, C1-C4alkylcarbonyl or C1-C3alkoxycarbonyl, or R7 is an alicyclic ring system; R2 is a group R88R89N—; R88 and R89 independently of one another are hydrogen, C1-C6alkyl, C1-C6alkyl substituted by halogen, CN, C1-C3alkoxy or C3-C12cycloalkyl, C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl or C6-C12bicycloalkyl substituted by C1-C3alkyl; and R3 is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.
8. A compound according to claim 7, in whichR7 is C3-C12cycloalkyl, C3-C12cycloalkyl substituted by halogen, CN, C1-C6alkyl, cyano-C1-C5alkyl, C1-C3alkoxy or C1-C3halogenoalkyl, or R7 C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by methyl, or R7 is C6-C12bicycloalkyl, C6-C12bicycloalkyl substituted by methyl, or chlorine, C6-C12bicycloalkenyl or C6-C12bicycloalkenyl substituted by methyl, or R100 and R101 are as defined in claim 7; or in which R20 is hydrogen or C1-C4alkyl; R21 and R22 independently of one another are hydrogen or C1-C4alkyl; R24 is hydrogen or methyl; R25 is hydrogen, chlorine, methyl or methoxy; R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2-halogenoalkoxy; n6 is 3, 4, 5 or 6; n9 is 3 or 4; and R100 and R101 are as defined above; R2 is a group R88R89N—; R88 and R89 independently of one another are hydrogen or C1-C6alkyl; and in which X is —O— or —S—; X2 is —O—, —S— or —NR100—; R20, R24 and R100 are as defined above; R92 is hydrogen or C1-C4alkyl; R93 is hydrogen, C1-C4alkyl, hydroxyl, C1-C4alkoxy or C1-C4alkylthio; R97 is hydrogen, halogen, NO2, CN, C3-C6cycloalkoxy, C1-C10alkyl, C1-C10alkyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyl, C3-C10alkenyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylcarbonyl, C1-C10alkylcarbonyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkoxycarbonyl, C1-C10alkoxycarbonyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylcarbonyloxy or C1-C10alkylcarbonyloxy substituted by halogen, CN, NO2, C1-C6-alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R97 is CHO, C3-C8cycloalkyl, C1-C4alkylthio, C3- or C4alkenylthio, (R94)2N—, (R95)2N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group the radicals R94 independently of one another are hydrogen, C1-C10alkyl, C3-C8cycloalkyl, C1-C10alkylcarbonyl or substituted or unsubstituted arylcarbonyl; the radicals R95 independently of one another are hydrogen, C1-C5alkyl or C3-C8cycloalkyl; n5 is a number from 5 to 12; and R98 is as defined above.
9. A compound according to claim 8, in which X and X2 are —O—.
10. A compound according to claim 6, in whichR1 is a group —NR90R91 or R90 and R91 independently of one another are C1-C12alkyl, C1-C12alkyl substituted by halogen, CN or C1-C3alkoxy, C6-C12bicycloalkyl, C6-C12bicycloalkenyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted by C1-C4alkyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by C1-C4alkyl; the radicals R20 independently of one another are hydrogen or C1-C4alkyl; n1 is 1, 2, 3, 4 or 5; n2 is 0, 1 or 2; and n3 is a number from 3 to 10; R2 is a group R88R89N—; R88 and R89 independently of one another are hydrogen or C1-C6alkyl and in which X is —O—, —S—, —SO— or —SO2—; X2 is —O—, —S— or —NR100—; R100 is hydrogen or C1-C3alkyl; R20 is as defined above; R24 is hydrogen or methyl; R92 is hydrogen or C1-C4alkyl; R93 is hydrogen, C1-C4alkyl, C1-C4alkoxy or C1-C4alkylthio; R97 is hydrogen, halogen, NO2, CN, C3-C6cycloalkoxy, C1-C10alkyl, C1-C10alkyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyl, C3-C10alkenyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6-alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylcarbonyl, C1-C10alkylcarbonyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkoxycarbonyl, C1-C10alkoxycarbonyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylcarbonyloxy or C1-C10alkylcarbonyloxy substituted by halogen, CN, NO2, C1-C6-alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R97 is CHO, C3-C8cycloalkyl, C1-C4alkylthio, C3- or C4alkenylthio, (R94)2N—, (R95)2N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group the radicals R94 independently of one another are hydrogen, C1-C10alkyl, C3-C8cycloalkyl, C1-C10alkylcarbonyl or substituted or unsubstituted arylcarbonyl; the radicals R95 independently of one another are hydrogen, C1-C5alkyl or C3-C8cycloalkyl; n5 is a number from 5 to 12; and R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3-alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy.
11. A compound according to claim 10, in whichR1 is a group —NR90R91 or R90 and R91 independently of one another are C1-C12alkyl, C1-C12alkyl substituted by halogen, CN or C1-C3alkoxy, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by methyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted by methyl; the radicals R20 independently of one another are hydrogen or methyl; n1 is 2, 3 or 4; n2 is 0 or 1; and n3 is 3, 4 or 5; R2 is a group R88R89N—; R88 and R89 independently of one another are hydrogen or C1-C3alkyl; and in which X is —O— or —S—; R97 is hydrogen, halogen, NO2, CN, C1-C10alkyl, C1-C10alkyl substituted by halogen, CN, NO2, C1-C6alkoxy or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyl, C3-C10alkenyl substituted by halogen, CN, NO2, C1-C6alkoxy or substituted or unsubstituted aryl or aryloxy, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy or substituted or unsubstituted aryl or aryloxy, C1-C10alkoxycarbonyl, C1-C10alkoxycarbonyl substituted by halogen, CN, NO2, C1-C6alkoxy or substituted or unsubstituted aryl or aryloxy, C1-C10alkylcarbonyloxy or C1-C10alkylcarbonyloxy substituted by halogen, CN, NO2, C1-C6alkoxy or substituted or unsubstituted aryl or aryloxy, or R97 is (R94)2N—, (R95)2N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl; the radicals R94 independently of one another are hydrogen, C1-C4alkyl, C3-C8cycloalkyl, C1-C5alkylcarbonyl or substituted or unsubstituted arylcarbonyl; and the radicals R95 independently of one another are hydrogen, C1-C3alkyl or C3-C6cycloalkyl.
12. A compound according to claim 2, selected from the group consisting of:3-amino-5-pentafluorophenoxy-1-(trans-3,3,5-trimethylcyclohexanolyl)thiatriazine; 3-amino-5-pentafluorophenoxy-1-[(N-cis-3,3,5-trimethylcyclohexyl)methylamino]thiatriazine; 3-amino-5-pentafluorophenoxy-1-octamethyleneimino-thiatriazine; 3-amino-5-pentafluorophenoxy-1-decahydroquinolyl-thiatriazine; 3-amino-5-pentafluorophenoxy-1-tetrahydroisoquinolyl-thiatriazine; and the compound of the formula
13. A process for the preparation of a compound according to claim 1, in which R1 is the group —OR7; R2 and R3 independently of one another are halogen, C1-C10alkoxy, C1-C10alkoxy substituted by halogen, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined in claim 1, or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R2 and R3 independently of one another are C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-X—, C6-C12bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined in claim 1, which comprises a procedure in which a1) 1,3,5-trichlorothiatriazine is converted with an alcohol of the formula XVII R7—OH (XVII), in which R7 is as defined in claim 1if appropriate in the presence of an equimolar amount of base and an inert organic solvent, into the compound of the formula VII in which R7 is as defined, and this compound is then either b1) reacted with a compound of the formula XXIII R14—X1H (XXIII), in which R14 is C1-C10alkyl, C1-C10alkyl substituted by halogen, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined in claim 1, or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyl or C3-C10alkenyl substituted by halogen, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C3-C5alkynyl, C3-C8cycloalkyl, C6-C12bicycloalkyl, heterocyclyl of the formula in which R24, R100 and R101 are as defined above, or alicyclyl, and X1 is oxygen or sulfur, in the presence of an equimolar amount of base and an inert organic solvent, or b2) converted with a compound of the formula XVI R12—X1H (XVI), in which R12 is an aryl, phthalidyl, biphenyl or heteroaryl radical; and X1 is oxygen or sulfur, in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula VI in which R3 is —X1—R12, and this compound is either c2) reacted with the compound of the formula XXIII R14—X1H (XXIII), in which R14 and X1 are as defined above, in the presence of an equimolar amount of base and an inert organic solvent, or c3) converted with the compound of the formula XVI R12—X1H (XVI), in which R12 and X1 are as defined above, in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula V in which R3 is —X1—R12 and R7, X1 and R12 are as defined above, and this compound is then d3) reacted with the compound of the formula XXIII R14—X1H (XXIII), in which R14 and X1 are as defined, in the presence of an equimolar amount of base and in an inert organic solvent, or the compound of the formula VII b3) is converted with 2 mol of compound of the formula XVI R12—X1H (XVI), in which R12 and X1 are as defined, in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V, and this compound is then reacted in a manner analogous to that described under d3), or a2) 1,3,5-trichlorothiatriazine is converted with a C6-C12bicycloalkyl epoxide, a C6-C12bicycloalkyl epoxide substituted by C1-C3alkyl or an epoxide of the formula XVIII or XIX in which the radicals R13 independently of one another are hydrogen, C3-C8alkenyl, C1-C14alkyl, C1-C14alkyl substituted by halogen, NO2, CN, C1-C5alkoxy, aryloxy or C1-C3alkoxycarbonyl; the radicals R23 independently of one another are hydrogen or C1-C6alkyl; n8 is a number from 3-10; and n11 is 1 or 2, in an inert organic solvent, into the compound of the formula VII in which R7 is C2-C16-β-chloroalkyl, C2-C16-β-chloroalkyl substituted by halogen, NO2, CN, C1-C5alkoxy, aryloxy or C1-C3alkoxycarbonyl, C5-C12-β-chlorocycloalkyl or C5-C12-β-chlorocycloalkyl substituted by C1-C6alkyl, and this compound is reacted further in a manner analogous to that described under b1); b2) and c2); b2), c3) and d3); or b3) and d3), or a3) 1,3,5-trichlorothiatriazine is reacted with an alcohol of the formula XVII R7—OH (XVII), in which R7 is C1-C10alkyl, C1-C10alkyl substituted by halogen, CN, NO2, C1-C5alkoxy, C1-C5alkylthio, C3-C6alkenyloxy, C1-C3alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined in claim 1, or substituted or unsubstituted aryl or aryloxy, C3-C10alkenyl, C3-C10alkenyl substituted by halogen, C1-C3alkoxy or substituted or unsubstituted aryl or aryloxy, C3-C5alkynyl, C3-C8cycloalkyl, C6-C12bicycloalkyl, a heterocyclic ring of the formula in which R100 and R101 are as defined above, or alicyclyl, if appropriate in an inert solvent in the presence of an eqimolar amount of base.
14. A process for the preparation of a compound according to claim 1, in which R1 is the group —OR7; R2 is a group R88R89N—, and R3 is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, which comprises a procedure in which c4) a compound of the formula VI in which R7 is as defined in claim 1 and R3 is as defined above, is reacted with an amine of the formula XIII, XIV or XV R88R89NH (XIII), in which R20, R88, R89, Y and n7 are as defined in claim 1, if appropriate in a solvent; or c3) the compound of the formula VI is first converted with a compound of the formula XVI R12—X1H (XVI), in which R12 is an aryl, phthalidyl, biphenyl or heteroaryl radical, and X1 is oxygen or sulfur, in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V in which R3 is —X1—R12 and R7, R12 and X1 are as defined, and d4) this is then reacted with an amine of the formula XIII, XIV or XV in a manner analogous to that described under C4); or in which a4) 1,3,5-trichlorothiatriazine is converted with an alcoholate of the formula XVII1 (R7O—O−)n M1+n (XVII1), in which R7 is as defined in claim 1; M1+n is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and n is 1, 2, 3 or 4, in the presence of an inert organic solvent, into the compound of the formula VII in which R7 is as defined, and b4) this is reacted with an amine of the formula XIII, XIV or XV R88R89NH (XIII), in which R20, R88, R89, Y and n7 are as defined in claim 1, if appropriate in a solvent, to give the compound of the formula VIII in which R2 and R7 are as defined, and c5) this is then reacted with a compound of the formula XVI R12—X1H (XVI), in which R12 is an aryl, phthalidyl, biphenyl or heteroaryl radical; and X1 is oxygen or sulfur, in a solvent in the presence of a tertiary amine and, if appropriate, another base.
15. A process for the preparation of a compound according to claim 1, in which R1 is a group —NR90R91 or R1 is in which the radicals R20 independently of one another are hydrogen, C1-C4alkyl or C1-C3alkoxy; R25 is hydrogen, chlorine, methyl or methoxy; R100 is hydrogen or C1-C3alkyl; Y1 is —O—, —S— or —NR30; R30 is hydrogen, methyl, C1-C3alkylcarbonyl or (C1-C3alkyl)2NCO; n1 is 1, 2, 3, 4 or 5; n2 is 0, 1 or 2; and n3 is a number from 3 to 10; R2 is a group R88R89N—, and R3 is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, which comprises a procedure in which e) a compound of the formula III in which R7 is as defined in claim 1 and R2 and R3 are as defined, is reacted with an amine of the formula XI or XII in which R90 and R91 are as defined in claim 1 and R11 is a cyclic radical onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, if appropriate in a solvent; or in which a5) 1,3,5-trichlorothiatriazine is converted with an amine of the formula XI or XII in which R90 and R91 are as defined in claim 1 and R11 is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, or with an amide of the formula XI, or XII1 in which R90, R91 and R11 are as defined; M2+n is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and n is 1, 2, 3 or 4, in the presence of an inert organic solvent and if appropriate a base, into the compound of the formula IX in which R1 is as defined, and b5) this is reacted with an amine of the formula XIII, XIV or XV R88R89NH (XIII), in which R20, R88, R89, Y and n7 are as defined in claim 1, if appropriate in a solvent, to give the compound of the formula X in which R1 and R2 are as defined, and c6) this is then reacted with a compound of the formula XVI R12-X1H (XVI), in which R12 is an aryl, phthalidyl, biphenyl or heteroaryl radical; and X1 is oxygen or sulfur, in a solvent in the presence of a tertiary amine and a further equivalent amount of base.
16. A process for the preparation of a compound according to claim 1, in which R1 is a group —OR7;R2 is a group R88R89N—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and R3 is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, which comprises a procedure in which a compound of the formula I, in which R1 is a group —OR7, in which R7 is other than in the end product; and R2 and R3 are as defined, is reacted with an alcohol of the formula XVII R7—OH (XVII), in which R7 is other than in the starting substance of the formula I, in the presence of an inert organic solvent and a catalytic or equimolar amount of base.
17. A compound of the formula VII in which R7 is as defined in claim 1.
18. A compound of the formula VI in which R7 is as defined in claim 1, R3 is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined in claim 1.
19. A compound of the formula V in which R7 is as defined in claim 1, R3 is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined in claim 1.
20. A compound of the formula VIII in which R2 is a group R88R89N—, and R7, R20, R88, R89, Y and n7 are as defined in claim 1.
21. A compound of the formula IX in which R1is a group R90R91N— or R90 and R91 are as defined in claim 1; and R11 is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, excluding the compounds
22. A compound of the formula X in which R1 is a group R90R91N— or and R2i s a group R88R89N—, and R20, R88, R89, R90, R91, Y and n7 are as defined in claim 1; and R11 is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, excluding the compounds wherein R01 is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl; R02 is ethyl or i-butyl, R03 is cyclohexyl or i-butyl; and R02 and R03 together with the nitrogen atom to which they are bonded, form a piperidine ring.
23. A herbicidal or plant growth-inhibiting composition, which comprises a compound according to claim 1, in a herbicidal or plant growth-inhibiting effective amount, and an inert carrier.
24. The composition according to claim 23, in which the compound comprises between 0.1% and 95% of the composition.
25. A method of controlling undesirable plant growth, which comprises applying to the plants, in a herbicidally effective amount, the compound according to claim 1 to the plants or their environment.
26. The method according to claim 25, wherein an amount of between 0.001 and 4 kg of the compound per hectare is applied to the plants.
27. A method of inhibiting plant growth, which comprises applying a compound according to claim 1 in an effective inhibiting amount to the plants or their environment.

Priority Claims (1)

Number	Date	Country	Kind
38/96	Jan 1996	CH

PCT Information

Filing Document	Filing Date	Country	Kind
PCT/EP96/05770		WO	00

Publishing Document	Publishing Date	Country	Kind
WO97/25318	7/17/1997	WO	A

US Referenced Citations (6)

Number	Name	Date	Kind
4316015	Hamprecht et al.	Feb 1982	A
4343648	Hamprecht et al.	Aug 1982	A
4426219	Hamprecht et al.	Jan 1984	A
4428766	Hamprecht et al.	Jan 1984	A
4472191	Hamprecht et al.	Sep 1984	A
4585472	Hamprecht et al.	Apr 1986	A

Foreign Referenced Citations (1)

Number	Date	Country
113 006	May 1975	DE

Non-Patent Literature Citations (10)

Entry
Schramm et al. Synthesis of 5-alkylamino-1-dialkylamino-3-chloro-1,2,4,6-thia. Z. Chem. 15(1) 19, 1975.*
Michalik et al. Sterochemical studies of heterocyclic compounds. J. Prakt. Chem 319(5), 739-44, 1977.*
M. Haake et al. Z. Naturforsch., vol. 43b, pp. 763-768, 1988, abstract in English language on front page; Front sheet of the Inaugural-Dissertation of W. Jurgler, Philipps-Universitat Marburg, Marburg/Lahn, 1988.
J. Greeves et al., J. Chem. Soc. (C), pp. 875-878, 1970.
M. Michalik et al., J.f.prakt. Chemie, vol. 319, No. 5, pp. 739-744, 1977, abstract in English language on front page; Wissenschaftliche Zeitschrift der Wilhelm-Pieck-Universitat Rostock, vol. 28(9), p. 855, 1979, summary in English language on p. 859.
R.T. Boere et al., J. Amer. Chem. Soc., vol. 111, pp. 1180-1185, 1989.
W. Reid et al.,Chem. Ber., vol. 121, pp. 383-386, 1988; ibid., E. Fischer, vol. 124, p. 1347, 1991; ibid., S.J. Chen, vol. 126, p. 2601, 1993.
W. Stork et al., Z. Chem. vol. 14(2), p. 471, 1974; ibid. vol.15(1), p. 19, 1975; ibid. (15(2), 57, 1975; ibid. 15(5), p. 193, 1974; ibid., vol. 15(13), 104, 1975, ibid., 16(12), p. 490, 1976; please note that the English language abstracts of the foregoing 6 Z. Chem. references are.
A. Kalman et al., J. Chem. Soc., Perkin Trans II, vol. 10, p. 1322-7, 1977.
A. Kalman et al., Acta Cryst. vol. 35(4), p. 860-6, 1979.

Herbicidal 1,2,4,6-thiatriazines

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Priority Claims (1)

PCT Information

US Referenced Citations (6)

Foreign Referenced Citations (1)

Non-Patent Literature Citations (10)