MXPA00012952A

MXPA00012952A - Method for producing anellated triazoles and new anellated triazoles and their use

Info

Publication number: MXPA00012952A
Application number: MXPA/A/2000/012952A
Authority: MX
Inventors: Schafer Peter; Hamprecht Gerhard; Menke Olaf; Reinhard Robert; Zagar Cyrill; Westphalen Karlotto; Otten Martina; Walter Helmut
Original assignee: Basf Aktiengesellschaft*
Priority date: 1998-07-03
Filing date: 2000-12-20
Publication date: 2001-09-07

Abstract

The invention relates to a method for producing anellated triazoles, according to which substituted N-aminoureas are reacted with formaldehyde or paraformaldehyde to obtain the corresponding methylene-imine compounds and these are then cyclized in the presence of catalytic quantities of acid or in the presence of a metal oxide to tetrahydro-4H-1,3,4-ox(or thia)diazines, after which the anellated triazoles are prepared using phosgene or a phosgene substitute. The invention also relates to new anellated triazoles obtained using the method provided for by the invention.

Description

"PROCEDURE TO PREPARE TRIANGLES RINGS, THE TRIKOLS RUBBED AS IS PREPARED AND THEIR UTILIZATION" Description The present invention relates to a process for preparing ringed triazoles of the formula I where the substituents have the following meanings: X-X C-0, C-S, C-SO, C-S02oC-NR '; V C = W2, R1 R2C - C (= W2) - or C (= W2) - C (= W2) W1, W2 oxygen or sulfur; RA hydrogen, hydroxy, COOH, COOR2, halogen, cyano, C (O) NRnR12, OR3, C, - C6 - alkyl, C, - C6 - haloalkyl, C3 - C6 - alkenyl, C3 - C6 - alkynyl, COR3, S (O) nR3 or C (O) SR2; • R1 hydrogen, hydroxy, halogen, CN, C, -C6-alkyl, C, -C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, COR3, CHO, OR3, COOR2, C (O) SR2, C (O) NRnR12; R2 hydrogen, C, -C6-alkyl, C, -C6-haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl; R3 C, -C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C, -C6-haloalkyl, C, -C6 -alkoxy-C, -C6 -alkyl, carboxyl- C ^ C ^ - alkyl, C, -C6-alkoxycarbonyl-C, -C6-alkyl, C, -C6-alkylthio-C, -C6-alkyl, C, -C6-alkylsulfinyl-C, -C6-alkyl, C , -C 6 -alkylsulfonyl-C, -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C, -C 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl-C. C6-alkyl, C3-C5-alkynyloxycarbonyl-C, -C6-alkyl, C3-C6-cycloalkoxy-C, -C6-alkyl, C3-C6-alkenyloxy-C, -C6-alkyl, C3-C6-alkynyloxy- C, -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C, -C 6 -alkyl, C 3 -C (l-20 haloalkenyloxy-C, -C 6 -alkyl, C 3 -C 6 -haloalkynyloxy-C, -C 6 -alkyl, C3 - C6 - C, - - cycloalkyl -, thioalkyl, C3 - C6 - alkenylthio - C, - C6 - alkyl, C3 - C6 - alkynylthio - C, - C6 - alkyl, cyano - C, - C6 - alkyl, C3 - C6 - halocyclo - C, - C6 - alkyl, halogen - C - C6 - alkenyl, C, - C (, - C3 - C - alkenyl - C - C6 - haloalkoxy - C3 - C6 - alkenyl, C, - ? j »« «- a ^ i-aa - * ^ MSÍ ^?« * a¡ < & g ^^ > -. A - ^ - tfca ^ g ^ -feSi < »« I and -t? _ C6-C3-C6-C6-alkenyl, C3-C6-haloalkynyl, C, -C6-C3-C6-alkynyl, C3-C6-haloalkoxyalkynyl, C, -C6-alkylthioalkynyl, C , - C6 - alkylcarbonyl, CHR, 6COR17, CHR16P (O) (OR17) 2, P (O) (OR! 7) 2, CHR'6P (S) (OR17) 2, CHR'6C (O) NR "R12, CHR, 6C (O) NH2, C, -C6-alkyl, which is substituted by phenoxy or benzyloxy, where the rings in turn can be substituted by halogen, C, -C4-alkyl or C, -C4 haloalkyl, benzyl which can be substituted by halogen, C, -C 4 -alkyl or C, -C 4 -haloalkyl or phenyl and pyridyl, which can be substituted by halogen, C, -C 4 -alkyl, C, -C 4 -haloalkyl or C, - C4 - alkoxy; • 10 m the value 0, 1, 2 or 3; n the value 0, 1 or 2; Q one of the radicals Q - 1 to Q - 7 twenty j jy ^^ y ^^^^ ¡g ^^^ with Y rl oxygen or sulfur; ^ Htffltfftfttl ^ R4 hydrogen or halogen; • R5 C, -C6-alkyl, C, -C6-haloalkyl, OCH3, SCH3, OCHF2, halogen, CN or N02; R6 hydrogen, C, -C6-alkyl, C, -C6-haloalkyl, halogen, OR10, S (0) n R10, COR'0, COOR10, C (O) SR10, SCH2C = CH, C (O) NR11 R '2, CHO, CH = CHCO - OR10, CO - ON = CRI3R14, N02, CN, NHS02R15, f NHS02NHR15, - C (R18) = C (R19) - CO - R20, - CH (R18) - CH (R19) ) - 10 CO - R20, - C (R18) = C (R19) - CO - N (R20, R21), - CH (R18) - CH (R19) - CO - N (R20, R21), - C ( R21) = N - OR22, - COOC (R23) (R24) - COOR25, - CO - N (R26) - OR22 or - C (OR27) = N - OR22; R7, R8 independently of one another, hydrogen, C, -C6 -alkyl, C, -C6 -haloalkyl or halogen; when Q is Q-2, Q-5 or Q-6, R7 and R8 can form with the C atom, to which they are attached, a group C = 0; R9 C, -C6-alkyl, C, -C6-haloalkyl, C, -C6-alkoxy, C, -C6-alkoxy-C, -Ct-alkyl, C2-C6-alkenyl or C2-C6-alkynyl; R10 one of the radicals indicated in R3; R ", R13 independently of each other, hydrogen or C, -C6-alkyl, R12, R'4 independently of each other, C, -C6-alkyl or phenyl, which can be^ fc to be substituted by halogen, C, -C 4 -alkyl, C, -C 4 -haloalkyl or C, -C 4 -alkoxy; R1 'and R12 can be a group - (CH2) 5 -, - (CH2) 4 - or - CH2CH2OCH; CH2 -, wherein each ring can be substituted by C.-C3-alkyl, or .phenyl or benzyl; R13 and R14 can also form, together with a C atom, to which they are attached, a C3-C8-cycloalkyl group; D Ri155 C, -C6-alkyl or C, -C6-haloalkyl; -rt R16 hydrogen or C, -C6-alkyl; R17 C, -C6 -alkyl, C2-C6-alkenyl or C2-C6-alkynyl; R18, R23, R24 in each case, hydrogen or C, -C3-alkyl; R19 halogen, cyano or methyl; R20 hydroxy, C, - C6 - alkoxy, C3 - C6 - cycloalkoxy, C, - C4 - alkoxy C, -C4-alkoxy, C, -C4-alkylthio-C, -C4-alkoxy, C, -C4 alkylsulfinyl-C, -C4-alkoxy, C, -C4-alkylsulfonyl-C, -C4 alkoxy, cyano-C , - C6 - alkoxy, C, - C4 - alkoxycarbonyl - C - C4 alkoxy, C3 - C6 - alkenyloxy, C3 - C6 - alkynyloxy, C, - C6 - partially or fully halogenated alkoxy, C3 - C6 - alkenyloxy partially or totally halogenated, C3-C6-partially or fully halogenated alkynyloxy, C, -C6-alkylthio, further C, -C6-alkoxy, which may carry two other substituents of C, -C6-alkoxy; R21 hydrogen, C, -C6 -alkyl or C, -C6 -halogenalkyl; R 22 hydrogen, C, -C 6 -alkyl, C, -C 4 -alkoxy-C, -C 4 -alkyl, C, -C 6 -halogenalkyl, C, -C 6 -cyanoalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-halogenalkynyl, carboxy-C, -C6 -alkyl, C, -C6-alkoxycarbonyl-C, -C4 -alkyl, C, -C6 -alkylcarbonyl-C, - C6-alkyl or C, -C6-alkylcarbonyloxy-C, -C6-alkyl; R25 hydrogen, C, -C6 -alkyl, C3-C6-cycloalkyl, C, -C6 -alkoxy-C, -C4 -alkyl, cyano-C, -C6 -alkyl, halogen-C, -C6 -alkyl, C3- C6-alkenyl or C3-C6-alkynyl; R26, R27 independently of one another, C, -C6 -alkyl, C, -C4 -alkoxy-C, -C4 -alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C, -C6 - halogenalkyl, C, -C 6 -cyanoalkyl, C 3 -C 6 -halogenalkenyl, C 3 -C 6 -halogenalkynyl or C, -C 6 -alkoxycarbonyl-C, -C 4 -alkyl; R26 also, hydrogen. Beyond this, the invention relates to novel ringed triazoles of the formula I ' where Z is oxygen, sulfur, SO or S02, its use in the protection of plants, as well as ringed triazoles of the formula I. "In addition, the invention relates to the substituted N-methyleneimino-N'-phenyluranes of the formula III ' where the substitutes have the following meanings: O, S, S = O or S02; • Halogen RA or C, -C3-alkyl; W1 oxygen or sulfur; R4 hydrogen or halogen; • R5 halogen, cyano or trifluoromethyl; R6 a group - C (R18) = C (R19) - CO - R20, - CH (R18) - CH (R19) - CO - R20, - C (R18) = C (R19) - CO - N (R20, R21), - CH (R18) - CH (R19) - CO - N (R20, R21) - C (R21) = N - OR22, - CO - OC (R23) (R24) - CO - OR 25 CO - N (R26) - OR22 or - C (OR27) = N - OR22; R18, R23, R24 in each case, hydrogen or C, -C3-alkyl; R19 halogen, cyano or methyl; twenty R20 hydroxy, C, -C6-alkoxy, C3-C6-cycloalkoxy, C, -C4-alkoxy-C, -C4-alkoxy, C, -C4-alkylthio-C, -C4-alkoxy, C, -C4-alkylsulfinyl - C, - C4 - alkoxy, C, - C4 - alkylsulfonyl - C, - C4 - alkoxy, cyano - C, - C6 - Alkoxy, C, -C-alkoxycarbonyl-C, -C4-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C, -C6-partially or fully halogenated alkoxy, C3-C6-alkenyloxy partially or wholly halogenated, C3-C6-partially or fully halogenated alkynyloxy, C, -C6-alkylthio, further C, -C6-alkoxy, which may carry two other substituents of C, -C6-alkoxy; R 21 hydrogen, C 1 -C 6 -alkyl or C, -C 6 -halogenalkyl; R22 hydrogen, C, -C6-alkyl, C, -C4-alkoxy-C, -C4 -alkyl, C, -Chalogenalkyl, C, -C6-cyanoalkyl, C3-C6-cycloalkyl, C3-C6 alkenyl, C3 - C6 - alkynyl, C3 - C6 - haloalkenyl, C3 - C6 haloalkynyl, carboxy - C, - C6 - alkyl, C, - C6 - alkoxycarbonyl Cj - C ^ alkyl, C, - C6 - alkylcarbonyl - C, - C6 - alkyl or C, -C6 • alkyl-carbonyloxy-C6-C6-alkyl; R25 hydrogen, C, -C6-alkyl, C3-C6-cycloalkyl, C ^ Cf, -alkoxy-C, -C4 -alkyl, cyano-C ^ C ^ alkyl, halogen-C, -C6 -alkyl, C3-C6 - alkenyl or C3-C6-alkynyl; R26, R27 C, -C6 -alkyl, C, -C4 -alkoxy-C, -C4 -alkyl, C3-Q-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C, -C6 -halogenalkyl, C , - C6 - cyanoalkyl, C3 - C6 - halogenalkenyl, C3 - C6 - halogenalkynyl or C, - C6 - alkoxycarbonyl - C, - C4 - alkyl, and R26 in addition, hydrogen; m 0, 1, 2 or 3, • and its use to prepare ringed trizards of the formula I '. EP-A 210 137 and WO 94/10173 describe ringed triazoles of herbicidal efficacy and processes for their preparation. According to the process described in WO 94/10173 N'-substituted derivatives of N-aminoureas of the formula II are converted with aldehydes in the presence of the acid to form tetrahydro-4 H-l, 3, 4-ox (or tia) substituted diazines of the formula IV and these are cyclized with phosgene or a phosgene substitute to form the compounds of the formula I. This process provides ringed triazoles only with a simple substitution of the phenyl and not with the desired yields.

There was a need to present a better method for preparing the ringed triazoles, especially for several times phenyl-substituted products, as described in WO 94/10173. Surprisingly it was found that the ringed triazoles of the formula I can be obtained in higher yields and with an improved purity, if N'-substituted derivatives of N-aminoureas of the formula II are transformed eleven US in a first step with formaldehyde or aqueous paraformaldehyde in the presence of acid in a neutral or slightly alkaline medium to form new N-methyleneimino-N'-substituted ureas of the formula III I, ***** cyclize in a second step by adding catalytic amounts of acid or a neutral or acidic surface metal oxide to form tetrahydro-4 H-1, 3, 4-ox (or thia) substituted diazines of the formula IV W1 and the latter are cyclized with phosgene or a phosgene substitute to form the compounds of formula I.

The denominations used in the definition of substituents represent collective nouns for individual enumerations of each member of the groups. All alkyl radicals can be • straight or branched chain. The halogenalkyl radical bears preferably one to five identical or different halogen atoms. As an example, the following are detailed: halogen is: fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine; lo-C.-C3-alkyl is: methyl, ethyl, n-propyl or 1-methylethyl; C, -C4-alkyl is: Cj-C3-alkyl as mentioned above, as well as n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl; fifteen C, -C6-alkyl is: C, -C4 -alkyl as mentioned above, as well as n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, - hexyl, 1,1-dimethyl-propyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-20-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- methylpropyl or 1-ethyl-2-methylpropyl; (C, -C6-alkyl) carbonyl is: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1 - ™ dimethylethylcarbonyl, n - pentylcarbonyl, - 1 - methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimeiyl-propylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 2, 2 >; - dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,], 1, 2-trimethylpropylcarbonyl, 1, 2, 2-trimethylpropylcarbonyl, 1-ethyl- • 1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, in particular is methylcarbonyl, ethylcarbonyl or 1-methylethylcarbonyl; C3-C4-alkenyl is: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethyl, n-buten-1-yl, n-buten-2-yl, n-buten - 3-yl, 1-methylprop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-mei.l-20 prop-2-en-1-lyo or 2 - methyl-prop-2-en-1-yl; C3-C6-alkenyl is: C3-C4-alkenyl as mentioned above, as well as n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4 - ilo, 1-methyl-but-1-en-1-yl, 2-methyl-but-25 1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methyl-but- 2-en-1-yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl- • but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl - prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1"-yl, 1-ethyl-prop-1-en-2-yl, 1-ethyl-prop-2 - en - 1 - yl, n - hex - 1 - en - 2 - yl, n - hex - 1 - en - 1 - yl, n - hex - 2 - en - 1 - yl, n - hex - 3 - en 1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methyl-pent-1 - en - 1 - yl, 3 - methyl - pent - 1 - en - 1 - • yl, 4 - methyl - pe nt-1-en-1-yl, 1-methyl-pent-2-en-1-yl, 2 -10 methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-1 - ilo, 4-methyl-pent-2-en-1-yl, 1-methyl-pent-3-en-1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-pent - 3-en-1-yl, 4-methyl-pent-3-en-1-yl, 1-methyl-pent-4-en-1-yl, 2-methyl-pent-4-en-1-yl , 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-yl, 1, 1- dimet: 1-but-2-en-yl, 1,1-dimethyl - but - 3 - en - - yl, 1,2 - dimet: 1 - but - 1 - en - yl, 1,2 - dimethyl - but - 2 - en - yl, 1,2 - dimet: 1 - but-3-en-yl, 1,3-dimethyl-but-1-en-yl, 1,3-dimet: 1-but-2-en-yl, 1,3-dimethyl-but-3 - en - - ilo, 2, 2 - 20 dimet: 1 - but - 3 - en - yl, 2, 3 - dimethyl - but - 1 - en - yl, 2, 3 - dimet: 1 - but - 2 - en - - ilo, 2, 3 - dimethyl - but - 3 - en - yl, 3,3 - dimet: 1 - but - 1 - en - yl, 3,3 - dimethyl - but - 2 - en - 1-yl, 1-ethyl-but-1-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl- but - 1 - en - 1 - yl, 2 - ethyl - but - 2 - en - 1 - yl, 2 - ethyl fifteen - ^ - Éi - áí ^ iÉ-tr-i-! - but - 3 - en - 1 - yl, 1, 1, 2 - trimethyl - prop - 2 - en - 1 - yl, 1 - et I - 1 - methyl - prop - 2 - en - 1 - yl, 1 - ethyl-2-methyl-prop-1-en-1-yl or 1-ethyl-2-methyl-prop-2-en-1-yl, preferably ethenyl or F prop-2-en-1-yl; C3 - C4 - alkynyl is: prop - 1 - in - 1 - yl, prop - 2 - in - 3 - yl, n - but - 1 - ih - 1 - yl, n - but - 1 - in - 4 - yl on-but-2-in-1-yl; C3 - C6 - alkynyl is: C3 - C4 - alkynyl as mentioned above • 1C above, as well as for example n-pent-1-in-1-yl, n-pent-1-in-3-yl, n-pent-1-in-4-yl, n-pent-1-in - 5 - ilo, n - pent - 2 - in - 1 - yl, n - pent - 2 - in - 4 - yl, n - pent - 2 - in - 5 - yl, 3 - methyl - but - 1 - in 1-yl, 3-methyl-but-1-yn-3-yl, 3-methyl-but-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1 - in - 3 - yl, n - hex - 1 - in - 15 4 - yl, n - hex - 1 - in - 5 - yl, n - hex - 1 - in - 6 - yl, n - hex - 2 - in-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn 1-yl, n-hex-3-yn-2-yl, 3-methyl-pent-1-yn-1-yl, 3-methyl-pent-1-yn-3-yl, 3-methyl-pent-yl 1-in-4-yl, 3-methyl-pent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl, 4-methyl-pent-2-yn-4-yl or 4-methyl-pent-2-yn-5-yl, in particular is prop-2-yn-1-yl or 1-methyl-prop-2-yn-1-yl; C3-C6-cycloalkyl-C, -C4-alkyl is: cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, 16 cyclooctylmethyl, 1- (cyclopropyl) ethyl, 1- (cyclobutyl) ethyl, 1- (cyclopentyl) ethyl, 1- (cyclohexyl) ethyl, 2- (cyclopropyl) ethyl, 2- (cyclobutyl) ethyl, 2- (cyclopentyl) ethyl , 2 - (cyclohexyl) ethyl, 2 - • (cyclopropyl) ethyl, 3 - (cyclopropyl) ethyl, 3 - (cyclopropyl) propyl, 3 - (cyclobutyl) propyl, 3 - (cyclopentyl) propyl, 3 - (cyclohexyl ) propyl, 4- (cyclopropyl) butyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl, 4 - (cyclohexyl) butyl, especially cyclopentylmethyl or cyclohexyl ethyl; C3-C6-cycloalkyl-C, -C6-alkyl is: cyclopropylmethyl, • 10-Cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, 1- (cyclopropyl) ethyl, 1- (cyclobutyl) ethyl, 1- (cyclopentyl) ethyl, 1- (cyclohexyl) ethyl, 2- (cyclopropyl) ethyl, 2- ( cyclobutyl) ethyl, 2- (cyclopentyl) ethyl, 2- (cyclohexyl) ethyl, 2- (cyclopropyl) propyl, 3- (cyclopropyl) propyl, 3- (cyclobutyl) propyl, 15 3 - (cyclopentyl) propyl, 3 - ( cyclohexyl) propyl, 2- (cyclopropyl) butyl, 3- (cyclopropyl) butyl, 4- (cyclopropyl) butyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl, 4 - (cyclohexyl) butyl, 2- (cyclopropyl) ) pentyl, 3 - (cyclopropyl) pentyl, 4 - (cyclopropyl) pentyl, 5 - (cyclopropyl) pentyl, 2 - (cyclobutyl) pentyl, 3 - (cyclobutyl) pentyl, 5 - (cyclobutyl) pentyl, 2- (cyclopropyl) hexyl, 3 - (cyclopropyl) hexyl, 6 - (cyclopropyl) hexyl, especially cyclopentylmethyl or cyclohexylmethyl; C3-C6-cycloalkoxy is: cyclopropoxy, cyclobutoxy, cyclopentoxy or cyclohexoxy; 25 C, - C4-alkoxy is: 0CH3, 0C2H5, 0CH2-C2H5, OCH (CH3), n-butoxy, 1-methylpropoxy, 2-methylpropoxy or OC (CH3) 3, especially is OCH3 or OC2H5; - . 5-Ci-Cg-alkoxy is: C, -C 4 -alkoxy as mentioned above, as well as for example-n-pentoxy, 1-methylbutoxy, 2-methylbutoxy. 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 - dimethylbutoxy, 1, 2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethyl-butoxy, 2,3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethyl-butoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, , 2, 2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, in particular is OCH 3, OC 2 H 5 or OCH (CH 3) 2; fifteen (C, -C6-alkoxy) carbonyl is: (C, -C4-alkoxy) carbonyl as mentioned above, as well as for example n-pentoxycarbonyl, 1-methyl-butoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl , 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-20-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methyl-pentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl , 1,2-dimethyl-25-butoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethyl-butoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethyl-butoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1, 1 2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl- • 1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular is methoxycarbonyl, ethoxycarbonyl or 1-methylethoxycarbonyl; cyano-C, -C6-alkyl is, for example, CH2CN, 1-cyanoet-1-yl, 2-cyano-et-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3 - cyano-prop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1 - • 10 cyano-but-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1 - ilo, 4 - cyanobut - 1 - yl, 1 - cyanobut - 2 - yl, 2 - cyanobut - 2 - yl, 1 - • cyanobut - 3 - yl, 2 - cyano - but - 3 - yl, 1 - cyano - 2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, in particular is CH2CN or 2-15 cyanoethyl; cyano-C, -C6-alkoxy is: 1-cyano-1-ethoxy, 2-cyano-1-ethoxy, 1-cyano-1-propoxy, 2-cyano-1-propoxy, 3-cyano-1-propoxy, 1-cyano-2-propoxy, 1-cyano-1-butoxy, 2-cyano-1-butoxy, 3-20 cyano-1-butoxy, 4-cyano-1-butoxy, 1-cyano-2-butoxy, 2 - cyano-2-butoxy, 1-cyano-3-butoxy, 2-cyano-3-butoxy, 1-cyano-2-methyl-3-propoxy, 2-cyano-2-methyl-3-propoxy, 3-cyano - 2-methyl-3-propoxy or 2-cyanomethyl-2-propoxy, in particular 2-cyano-1-ethoxy or 3-cyano-1-propoxy; 25 C, -C6-halogenalkyl is: C, -C4-alkyl as mentioned above, which is partially or totally substituted by fluorine, chlorine and / or bromine, ie for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl , trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-chloroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2 - difluoroethyl, 1-chloro-1,2,2-trifluoroethyl, 2,2-dichloro-2-fluoroethyl, 1,2,2-trifluoroethyl, 2, 2,2-trichloroethyl, pentafluoroethyl or 3-chloropropyl, preferably trifluoromethyl; C3-C6-halogenalkenyl is: C3-C6-alkenyl as mentioned above, which is partially or totally substituted by fluorine, chlorine and / or Bromine, ie by way of example 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3, 3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoalyl, 3 - bromoazol, 2, 3-dibro alilo, 3, 3-dibromalilo, 2, 3, 3 - tribromalilo or 2, 3 - dibrom - but - 2 - enilo, especially is 2 - chloroalilo or 3, 3 - dichloro - alilo; twenty C3-C6-halogenalkynyl is: C3-C6-alkynyl as mentioned above, which is partially or totally substituted by fluorine, chlorine and / or bromine, ie for example 3-chloropropargyl, 3-bromopropargyl, 3-fluoropropargyl, 3, 3, 3 - trifluoropropargyl, 4-chloro-but-2 - 25 twenty £ & _ £ *. 8 inyl, 4-bromo-but-2-ynyl, 4, 4, 4-trifluorobut-2-ynyl, 1,4-dichloro-but-2-ynyl, 5-chloro-pent 3-inyl, 5-fluoro-pent-3-ynyl, 5, 5, 5-trifluoro-pent-3-ynyl, 6-chloro-hex-2-ynyl, • preferably 3-chloropropargyl, 3, 3, 3-trifluoropropargyl, 4, 4, 4-trifluoro-but-2-ynyl; C. - C4 - halogenalkoxy is: a C, -C4-alkoxy radical as mentioned above, which is partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie for example OCH2F, OCHF2, OCF3, • 10 0CH2C1, OCH (Cl) 2, OC (Cl) 3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloro-ethoxy, 2-bromoethoxy, 2-Iodetoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy , 2, 2 - difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3, 3,3-trifluoropropoxy, 3, 3, 3-trichloropropoxy , OCH2-C2F5, OCF2-C2F5, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2,20-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4- bromobutoxy or nonafluorobutoxy, especially 2-chloroethoxy or 2,2,2-trifluoroethoxy; C, -C6-halogenalkoxy is: a C, -C6-alkoxy radical as mentioned above, which is partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie for example a radical mentioned in C, - C4 - halogenalkoxy or is 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5, 5, 5-trie! gold f ^ - 1 - pentoxy, undecafluoropentoxy, 6 - fluoro - 1 - hexoxy, 6 - chloro • 1 - hexoxy, 6 - bromo - 1 - hexoxy, 6 - Iod - 1 - hexoxy, 6, 6, 6 - trichloro - 5-hexoxy or dodecafluorohexoxy, in particular is OCH2F, OCHF2, OCF3, OCH2Cl, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy; I C3-C6-alkenyloxy is: prop-1-en-1-yloxy, prop-2-en-1-yloxy, 10-methylenynyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n- buten-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1-yloxy, 2 - methyl-prop-2-en-1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but- 1-en-1-yloxy, 2-methyl-but-15 1-en-1-yloxy, 3-methyl-but-1-en-1-yloxy, 1-methyl-but-2-en-1-yloxy , 2-methyl-but-2-en-1-yloxy, 3-methyl-but-2-en-1-yloxy, 1-methyl-but-3-en-1-yloxy, 2-methyl-but-3 - en-1-yloxy, 3-methyl-but-3-en-1-yloxy, 1, 1-dimethyl-prop-2-en-1-yloxy, 1, 2-dimethyl-prop-1-en-1 - iloxy, 1, 2-dimethyl-prop-2-en-1-yloxy, 1-ethyl-prop-1-en-2-yloxy, 1-ethyl-prop-2-en-1-yloxy, n - hex - 1 - in 1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex-5-en-1 - iloxy, 1-methyl-1-pent-1-en-1-yloxy, 2-methyl-pent-1-en-1-yloxy, 3-methyl-pent-1-en-1-yloxy, 4-methyl- pent-1-en-1-yloxy, 1-methyl-25 pent-2-en-1-yloxy, 2-methyl-pent-2-en-1-yloxy, 3-methyl-pent-2-en-1-yloxy, 4-methyl-pent-2-en-1 - Iloxy, 1-methyl-pent-3-en-1-yloxy, 2-methyl-pent-3-en-1-yloxy, 3-methyl- • pent-3-en-1-yloxy, 4-methyl-pent - 3-en-1-yloxy, 1-methyl-pent-4-en-1-yloxy, 2-methyl-pent-4-en-1-yloxy, 3 - "methyl-pent-4-en-1 - Iloxy, 4-methyl-pent-4-en-1-yloxy, 1, 1-dimethyl-but-2-en-1-yloxy, 1,1-dimethyl-but-3-en-1-yloxy, 1, 2-dimethyl-but-1-en-1-yloxy, 1, 2-dimethyl-but-2-en-1-yloxy, 1, 2-dimethyl-but-3-en-1-yloxy, 1, 3 - dimethyl-but-1-en-1-yloxy, • 10 1, 3-dimethyl-but-2-en-1-yloxy, 1,3-dimethyl-but-3-en-1-yloxy, 2,2-dimethyl-but-3-en-1-yloxy, 2, 3-dimethyl-but-1-en-1-yloxy, 2,3-dimethyl-but-2-en-1-yloxy, 2,3-dimethyl-but-3-en-1-yloxy, 3, 3-dimethyl-but-1-en-1-yloxy, 3, 3-dimethyl-but-2-en-1-yloxy, 1-ethyl-but-1-en-1-yloxy, 1-ethyl-but- 2-in-15 1-iloxy, 1-ethyl-but-3-en-1-yloxy, 2-ethyl-but-1-en-1-yloxy, 2-ethyl-but-2-en-1-yloxy , 2-ethyl-but-3-en-1-yloxy, 1, 1, 2-trimethyl-prop-2-en-1-yloxy, 1-ethyl-1-methyl-prop-2-en-1-yloxy , 1-ethyl-2-methyl-prop-1-en-1-yloxy or 1-ethyl-2-methyl-prop-2-en-1-yloxy, preferably ethenyloxy or prop-2-en-1-yloxy; C3 - C6 - alkynyloxy is: propargyloxy, prop - 1 - in - 1 - oxy, but - 1 - in - 3 - oxy, 3 - methyl - but - 1 - in - 3 - oxy, 3, 3 - dimethyl - but - 1 - in - 4 - oxy, pent - 1 - in - 3 - oxy, 3 - methyl - pent - 1 - in - 3 - oxy, hex - 3 - in - 25 ^ T ^^^^^^^^^^^^^^^^ j ^^^^^ 5-oxy, especially propargyloxy, but-1-in-3-oxy or 3-methyl-but-1 - in -3-oxy; • C, -C6-alkylthio-Cf-^ -alkoxy is: C, -C6-substituted alkoxy-C, -C6-alkylthio as mentioned above, ie for example is methylthiomethoxy, ethylthiomethoxy, n-propylthio-methoxy , (1-methylethyl) methoxy, n-butylthiomethoxy, (1-methylpropylthio) methoxy, (2-methylpropylthio) methoxy, (1,1-dimethylethylthio) methoxy, 2- (methylthio) ethoxy, 2- (ethylthio) ethoxy, - (n-propylthio) ethoxy, 2- (1-methylethylthio) ethoxy, 2- (n-butylthio) ethoxy, 2- (1-methylpropylthio) ethoxy, 2- (2-methylpropylthio) ethoxy, 2- (1, 1) - dimethylethylthio) ethoxy, 2- (methylthio) propoxy, 2- (ethylthio) propoxy, 2- (n-propylthio) propoxy, 2- (1-methylethylthio) -propoxy, 2- (n-butylthio) propoxy, 2 - ( 1-methylpropylthio) -propoxy, 2- (2-methylpropylthio) propoxy, 2 - (1, 1 - dimethylethylthio) propoxy, 3 - (methylthio) propoxy, 3 - (ethylthio) propoxy, 3 - (n -propylthio) propoxy, 3- (1-methylethylthio) propoxy, 3 - (n-butylthio) ) propoxy, 3- (1-methylpropylthio) propoxy, 3- (2-methylpropylthio) propoxy, 3- (1,1-dimethylethylthio) propoxy, 2- (methylthio) butoxy, 2- (ethylthio) butoxy, 2- (n - propylthio) butoxy, 2- (1-methylethylthio) butoxy, 2- (n-butylthio) butoxy, 2- (1-methylpropylthio) butoxy, 2- (2-methylpropylthio) butoxy, 2- (1,1-dimethylethylthio) - butoxy, 3- (methylthio) butoxy, 3- (ethylthio) butoxy, 3- (n-propylthio) butoxy, 3- (1-methylethylthio) butoxy, 3- (n-butylthio) butoxy, 3- (1-methylpropylthio) ) butoxy, 3- (2-methylpropylthio) butoxy, 3- (1,1-dimethylethylthio) -butoxy, 4- (methylthio) butoxy, 4- (ethylthio) butoxy, 4- (n- 24 propylthio) butoxy, 4- (1-methylethylthio) butoxy, 4- (n-butylthio) butoxy, 4- (1-methylpropylthio) butoxy, 4- (2-methylpropylthio) butoxy, 4- (1,1-dimethylethylthio) butoxy , 5 - (methylthio) pentoxy, 5 - (ethylthio) pentoxy, 5 - (n - • propylthio) pentoxy, 5- (1-methylethylthio) pentoxy, 5- (n-butylthio) pentoxy, 5- (1-methylpropylthio) pentoxy, 5- (2-methylpropylthio) pentoxy, - (1, 1 - dimethylethylthio) - pentoxy, 6 - (methylthio) hexoxy, 6 - (ethylthio) hexoxy, 6 - (n -propylthio) hexoxy, 6 - (1-methylethylthio) hexoxy, 6 - (n-butylthio ) hexoxy, 6- (1-methylpropylthio) hexoxy, 6- (2-methylpropylthio) hexoxy or 6- (1,1-dimethylethylthio) hexoxy, especially methylthiomethoxy? oo ethylthioethoxy; -, C, - C6 - alkylthio is: SCH3, SC2H5, SCH2 - C2H5, SCH (CH3) 2, n - butylthio, SCH (CH3) - C2H5, 2 - methylpropylthio, 1, 1 - dimethylethylthio, n - pentthylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio, especially is SCH3 or SC2H5; C, -C6-alkylthio-C, -C6-alkyl is: C, -C6-alkyl substituted by ^^ g ^ a j ^ g ¿¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡ - Cg-alkylthio as mentioned above, ie for example is methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, (1-methyl-ethylthio) methyl, n-butyl-thiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, ( 1,1-dimethyl-ethylthio) methyl, 2-methylthioethyl. 2-ethylthioethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2 - (1,1-dimethylethylthio) ethyl, 2- (methylthio) propyl, 3- (methylthio) propyl, 2- (ethylthio) -propyl, 3- (ethylthio) propyl, 3- (propylthio) propyl, 3- (butylthio) ) propyl, 4- (methylthio) butyl, 4- (ethylthio) butyl, A - (n-propylthio) butyl or 4- (n-butylthio) butyl, especially is 2- (methylthio) ethyl; C, -C 4 -alkylsulfonyl is: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1, 1-dimethylethylsulfonyl, especially methylsulfonyl or ethylsulfonyl; C, -C6-alkylsulfonyl is: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethylethylsulfonylc, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethyl-propylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethyl-propylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2 - 26 ^^ i-. te - ^ - g- ^ *, "_É ^ ^ _ i ^ s ^ fe ^^^^^ methylpentylsulfonyl, 3-methyl-pentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl , 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-"- .. < t a n i methylpropylsulfonyl, especially methylsulfonyl; < # < C, -C4-alkylsulfinyl is: methylsulfinyl, ethylsulphinyl, n -.-propylsulfinyl, 1-methylethylsulphinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulphinyl, especially methylsulfinyl or ethylsulphinyl; Ci-C6-alkylsulfinyl is: methylsulfinyl, ethylsulfinyl, n-15 propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylplsulfinyl, 2-methylplsulfinyl, 1,1-dimethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethyl-plsulfinyl, , 2-dimethylplsulfinyl, 2,2-dimethyl-20-plsulfinyl, 1-ethylplsulfinyl, n -hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methyl-pentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2- dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3, 3 27 jgi j ^^ ^^^ »^ ¿^^^^? dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, in particular is methylsulfinyl; C, -C 4 -alkoxy-C, -C 4 -alkyl is: C, -C 4 -alkyl substituted by C, - C4 - alkoxy such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1 - . 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, ie for example is CH 2 OCH 3, CH 2 OC 2 H 5, n-propoxymethyl, (1-methylethoxy) methyl, n-butoxymethyl, (1-methylpropoxy) -methyl, (2-methylpropoxy) ) - methyl, (1,1-dimethylethoxy) methyl, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2 - . 2 - . 2 - (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2 - (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n -propoxy) propyl, 2- (1-methylethoxy) propyl, 2- (n-butoxy) propyl, 2 - (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy) propyl, 3 - (methoxy) propyl, 3 - (ethoxy) propyl, 3 - (n -propoxy) ) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3 - . 3 - (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1, 1 •• dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n -propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1) - methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1,1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n -propoxy) butyl, 3 - (1-methylethoxy) butyl, 3- (n-butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethoxy) butyl, 4 - (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1 • - methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1, 1-dimethylethoxy) butyl, preferably n-propoxymethyl, (1-methylethoxy) methyl, 2- (n-propoxy) ethyl or 2 - ( 1-methylethoxy) ethyl as well as particularly preferably CH 2 OCH 3, CH 2 OC 2 H 5, 2-methoxyethyl or 2-ethoxyethyl; f? o - Cj-C6-C6-alkoxy-C6-alkyl is: C, -Cg-alkyl substituted by C, -C6-alkoxy as mentioned above, ie for example is methoxymethyl, ethoxymethyl, n- propoxymethyl, (1-methylethoxy) methyl, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1,1-dimethylethoxy) methyl, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2 - (n-15 propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2 - (1 , 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) propyl, F 2 - (1-methylethoxy) propyl, 2- (n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-20 dimethylethoxy) propyl, - (methoxy) propyl, 3- (ethoxy) -propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3 - (2-methylpropoxy) propyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n- propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1,1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3-i'n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) butyl, 3 - (1 ^^ - methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethoxy) butyl, 4 - (methoxy) butyl, 4 - (ethoxy) butyl, 4 - | n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1,1-dimethylethoxy) butyl, especially is methoxymethyl or 2-methoxyethyl; C, -C 4 -alkoxy-C, -C 4 -alkoxy is: C, -C 4 -alkoxy substituted by C, - C4 - alkoxy such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1, 1-dimethylethoxy, ie for example is OCH2OCH3, OCH2OC2H5, n-propoxy-methoxy , (1-methylethoxy) methoxy, n-butoxymethoxy, (1-methyl-propoxy), - methoxy, [2- 15 methylpropoxy) -methoxy, (1,1-dimethyl-ethoxy) methoxy, 2 - (methoxy) ethoxy, 2 - (ethoxy) ethoxy, 2 - (n-propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2 - (n-butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2 - (1,1-dimethyl-ethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (n-propoxy) propoxy, 2- (1-methylethoxy) -propoxy, 2 - (n-20-butoxy) propoxy, 2- (1-methylpropoxy) propoxy, 2- (2-methylprop- cyxy) propoxy, 2- (1, 1-dimethylethoxy) propoxy, 3 - (methoxy) propoxy, 3- (ethoxy) propoxy , 3 - (n-propoxy) propoxy, 3- (1-methyletoxy) propoxy, 3 - (n-butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-25 methylpropoxy) propoxy, 3 - ( eleven - dimethylethoxy) propoxy, 2 - (methoxy) butoxy, 2- (ethoxy) butoxy, 2- (n-propoxy) butoxy, 2- (1-methylethoxy) butoxy, 2- (n-butoxy) -butoxy, 2- (1-methylpropoxy) butoxy, 2- (2 - methylpropoxy) butoxy, 2- (1, 1-dimethylethoxy) butoxy, 3 - (methoxy). • butoxy, 3- (ethoxy) butoxy, 3- (n-propoxy) butoxy, 3- (1-methylethoxy) butoxy, 3- (n-butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3 - (2 - methylpropoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4 - (methoxy) butoxy, 4 - (ethoxy) butoxy, 4 - (n-propoxy) butoxy, 4- (1-methylethoxy) butoxy, 4 - (n-butoxy) butoxy, 4- (1-methylpropoxy) butoxy, 4- (2 - • ""> methylpropoxy) butoxy or 4- (1,1-dimethylethoxy) butoxy, preferably f? on - propoxymethoxy, (1) - methylethoxy) methoxy, 2 - (n-propoxy) ethoxy or 2 - (1-methylethoxy) -ethoxy and also of special preference OCH2OCH3, OCH2OC2H5, 2-methoxyethoxy or 2-ethoxyethoxy; C. C6-C6-alkoxy-C6-alkoxy is: Cj-C6-alkoxy substituted by C, -15 C6-alkoxy as mentioned above, ie for example is methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, ( 1-methylethoxy) methoxy, n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1,1-dimethylethoxy) methoxy, 2- (methoxy) ethoxy, 2- (ethoxy) ethoxy, 2 - ( n-propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2 - (n-butoxy) ethoxy, 2- (1-20 methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2 - (1, 1 - dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (n-propoxy) propoxy, 2- (1-methylethoxy) propoxy, 2- (n-butoxy) propoxy, 2- (1 - methylpropoxy) propoxy, 2- (2-methylpropoxy) propoxy, 2 - (1, 1 - dimethylethoxy) propoxy, 3 - (methoxy) -propoxy, 3 - (ethoxy) propoxy, 3 - (n - propoxy) propoxy, 3- (1-methyletoxy) propoxy, 3 - (n-butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- (1,1-dimethylethoxy) Propoxy, 2 - (methoxy) butoxy, 2 - (ethoxy) butoxy, 2 - (n-propoxy) butoxy, 2- (1-methylethoxy) butoxy, 2- (n-butoxy) -butoxy, 2- (1-methylpropoxy) ) butoxy, 2- (2-methylpropoxy) butoxy, 2- (1,1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy) -butoxy, 3- (n-propoxy) butoxy, 3 - ( 1-methylethoxy) butoxy, 3- (n-butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3- (2-methyl-propoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4 - (methoxy) ) - butoxy, 4 - (ethoxy) butoxy, 4 - (n - ^ propoxy) butoxy, 4- (1-methyl-ethoxy) butoxy, 4 - (n-butoxy) butoxy, 4- (1-methylpropoxy) butoxy, 4 - (2-methylpropoxy) butoxy, 4- (1, dimethylethoxy) butoxy, 5- (methoxy) pentoxy, 5 - (ethoxy) pentoxy, 5- (n-propoxy) pentoxy, 5- (1-methylethoxy) pentoxy, 5 - (n-butoxy) pento < i. 5 - (1-methylpropoxy) pentoxy, 5- (2-methylpropoxy) pentoxy, 5- (1, -dimethylethoxy) pentoxy, 6 - (methoxy) hexoxy, 6 - (ethoxy) hexoxy, 6 - (n-propoxy) hexoxy , 6 - (1-methylethoxy) hexoxy, 6 - (n-butoxy) hexoxy, 6 - (1-methylpropoxy) hexoxy, 6 - (2-methylpropoxy) hexoxy or 6 - (1,1-dimethylethoxy) hexoxy, in particular is methoxymethoxy or ethoxymethoxy; carboxy - C, - C6 - alkyl is: C ^ Cf, - alkyl substituted by carboxy as mentioned above, ie for example carboxymethyl or, 2-carboxy-1-ethyl, 3-carboxy-1-propyl , 1-carboxy-1-ethyl, 1-carboxy-1-propyl, 3-carboxy-2-propyl, 2-carboxy-2-propyl. 1-carboxy-1-butyl, 1-carboxy-2-butyl, 2-carboxy-2-butyl D, 32-carboxy-1-butyl, 4-carboxy-2-butyl, 5-carboxy-1-pentyl, 5-carboxy-2-pentyl, 5-carboxy-3-pentyl, 5-carboxy-1-hexyl, especially carboxymethyl, 2-carboxy-1-ethyl or 1-carboxy- • 1-ethyl; (C-C6-alkoxy) carbonyl-C, -C2-alkyl is: C, -C2-alkyl substituted by (C, -C6-alkoxy) carbonyl as COOCH3, COOC2H5, n-propoxycarbonyl, COOCH (CH3) 2, n -butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl, COOC (CH3) 3, n -f 10-pentoxycarbonyl, 1-methyl-butoxycarbonyl and n-hexoxycarbonyl, ie for example is CH2-COOCH3, CH2-COOC2H5, n-propoxycarbonyl-methyl, CH2-COOCH (CH3) 2, n-butoxycarbonylmethyl, (1-methylpropoxycarbonyl) methyl, (2-methylpropoxycarbonyl) methyl, CH2-COOC ( CH 3) 3, n-15-pentoxycarbonylmethyl, (1-methylbutoxycarbonyl) -methyl, n-hexoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl, 1- (ethoxycarbonyl) ethyl, 1- (n-propoxycarbonyl) ethyl, 1- (1-methylethoxycarbonyl) ) ethyl, 1- (n-butoxycarbonyl) ethyl, 1- (n-pentoxycarbonyl) ethyl, 1- (1-methylbutoxycarbonyl) ethyl, 1- (n-hexoxycarbonyl) ethyl, 2-20 (methoxycarbonyl) -ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-propoxycarbonyl) ethyl, 2- (1-methylethoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, 2- (1-methylpropoxycarbonyl) ethyl, 2- (2-methylpropoxycarbonyl) ethyl, 2 - (1,1-dimethylethoxycarbonyl) ethyl; (C, -C6-alkoxy) carbonyl-C, -C4-alkyl is: (C, -C6-alkoxy) carbonyl-C, -C2-alkyl as mentioned above, as well as 2- (methoxycarbonyl) propyl , 2- (ethoxycarbonyl) propyl, 2- (n-F ~ propoxycarbonyl) propyl, 2- (1-methylethoscarbonyl) propyl, 2- (n-butoxycarbonyl) propyl, 2- (1-methylpropoxycarbonyl) -propyl, 2- ( 2-methylprppoxycarbonyl) propyl, 2- (1,1-dimethylethoxycarbonyl) propyl, 3- (methoxycarbonyl) propyl, 3- (ethoxycarbonyl) propyl, 3- (n-propoxycarbonyl) propyl, 3- (1-methylethoxycarbonyl) propyl, - (n-butoxycarbonyl) propyl, 3- (1-methylpropoxycarbonyl) propyl, 3- (2-or methylpropoxycarbonyl) propyl, 3- (1,1-dimethylethoxycarbonyl) propyl, 2- (methoxycarbonyl) butyl, 2- (ethoxycarbonyl) butyl, 2- (n-propoxycarbonyl) butyl, 2- (1-methylethoxycarbonyl) butyl, 2- (n-butoxycarbonyl) butyl, 2- (1-methylpropoxycarbonyl) butyl, 2- (2-methylpropoxycarbonyl) butyl, 2- ( 1, 1 - dimethyleth xicarbonyl) butyl, 3-15 (methoxycarbonyl) butyl, 3- (ethoxycarbonyl) butyl, 3- (n-propoxycarbonyl) butyl, 3- (1-methylethoxycarbonyl) butyl, 3- (r -butoxycarbonyl) butyl, 3- (1 - methylpropoxycarbonyl) butyl, 3 -. { 1-metipropoxycarbonyl) butyl, 3- (1, 1-dimethylethoxycarbonyl) butyl, - - (methoxycarbonyl) butyl, 4- (ethoxycarbonyl) butyl, 4- (n-20 propoxycarbonyl) butyl, 4- (1-methylethoxycarbonyl) butyl , 4 - (n-butoxycarbonyl) butyl, 4- (1-methylpropoxycarbonyl) butyl, 4- (2-methylpropoxycarbonyl) butyl or 4- (1,1-dimethylethoxycarbonyl) butyl, preferably CH2-COOCH3, CH2-COOC2H5, 1 - (methoxycarbonyl) ethyl, 2-methoxycarbonyl) ethyl or 1 - (ethoxycarboni) -ethyl; 3. 4 (C, -C6-alkoxy) carbonyl-C, -C6-alkyl is: C, -C6-alkyl substituted by (C, -C6-alkoxy) carbonyl as mentioned above • above, ie for example is methoxycarbonylmethyl, ethoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 4- (methoxycarbonyl) butyl, 5- ( methoxycarbonyl) pentyl or 6- (methoxycarbonyl) hexyl; (C, -C6-alkoxy) carbonyl-C-C4-alkoxy is: C, -C6-alkoxy substituted by (C, -C6-alkoxy) carbonyl as mentioned above, ie for example is methoxycarbonyl- methoxy, ethoxycarbonylmethoxy, n-propoxycarbonyl-methoxy, n-butoxycarbonyl-methoxy, 1- (methoxycarbonyl) ethoxy, 2- (methoxycarbonyl) ethoxy, 2-15 (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- ( n-butoxycarbonyl) ethoxy, 3- (methoxycarbonyl) propoxy, 3- (ethoxycarbonyl) propoxy, 3- (n-propoxycarbonyl) propoxy, 3 - (n-butoxycarbonyl) • propoxy, 4- (methoxycarbonyl) butoxy, 4- (ethoxycarbonyl) butoxy, 4- (n-propoxycarbonyl) butoxy, 4- (n-butoxycarbonyl) butoxy, 1-20 (ethoxycarbonyl) ethoxy, 1 - (propoxycarbonyl) ethoxy, 2 - (methoxycarbonyl) -2-propoxy, 2- (ethoxycarbonyl) -2-propoxy, 2-methyl-2 - (methoxycarbonyl) -2-propoxy, especially is methoxycarbonylmethoxy, 2-methoxycarbonyl-ethoxy or 1- (methoxycarbonyl) ethoxy; C3-Cg-alkenyloxy-C, -C6-alkyl is: Ct-C6-alkyl substituted by C3-C6-alkenyloxy as mentioned above, preferably allyloxy, 2-methylprop-2-en-1-yloxy, but- 1-er-3-yloxy, but-1-en-4-yloxy or but-2-en-1-yloxy, that is, a! example way / is allyloxymethyl, 2-allyloxyethyl or but-1-en-4-yloxymethyl; C3-C6-C, -C6-alkynyloxy-alkyl is: C, -C6-alkyl substituted by C3-C6-alkynyloxy as mentioned above, preferably propargyloxy, but-1-in-3-yl-oxy, but - 1-in-4-yloxy or but-2-yn-1-yloxy, i.e. by way of example, is' propargyloxymethyl or 2-propargyloxyethyl; C3-C6-cycloalkoxy-C, -C4-alkyl is: cyclopropyloxymethyl, cyclobutyloxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, 1- (cyclopropyloxy) ethyl, 1- (cyclobutyloxy) ethyl, 1- (cyclopentyloxy) ethyl, 1- (cyclohexyloxy) ethyl, 2- (cycloploxy) ethyl, 2- (cyclobutyloxy) ethyl, 2- (cyclopentyloxy) ethyl, 2- (cyclohexyloxy) ethyl, 3- (cycloploxy) pl, 3 - (cyclobutyloxy) pl, 3- (cyclopentyloxy) pl, 3- (cyclohexyloxy) pl, 4 - (cycloploxy) butyl, 4 - (cyclobutyloxy) butyl, 4 - (cyclopentyloxy) butyl or 4 - (cyclohexyloxy) butyl, in special is cyclopentyloxymethyl, cyclohexyloxymethyl or 2- (cyclopentyloxy) ethyl. The derivatives of the N'-substituted N-aminoureas of the formula II used as inputs in the processes according to the invention as well as the processes for their preparation are known per se and are described in the literature, for example in WO 94/10173 , so that • here reference is made to this corresponding bibliography for more details. Next, the reaction conditions and the carrying out of the process are described, taking as reference the preparation of the new ringed triazoles of the formula I '; but the data are taken to prepare all the compounds of the formula I according to claim 1. When applying the process according to the invention to prepare the compounds according to the invention of the formula I 'in good yields and with high purity, the following scheme: In a first step, the substituted N-amino-N '-phenylureas of the formula II' 15 R4 are transformed twenty where Z = means oxygen or sulfur, 25 37 - ^ au- ^^ gc ^ g ^^ jgj ^^^^ ^^^^^^^^^^^^^^^^^^^^^^ gg ^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ RA, W, R4, R5 and R6 have the meanings mentioned above, and m = means 0, 1 or 2, with formaldehyde or aqueous paraformaldehyde to liberate the acid, to form the new N-methyleneimino-N'-phenylureas of the formula IIP These are then cyclized in the presence of acid or an oxide of neon: to the neutral or acidic surfactant to form the 4 - (phenylcarbamoyl) -tetrahydro-4H-1, 3, 4-ox (or thia) diazines of Formula IV and the latter are cyclized with phosgene or a phosgene substitute to form the compounds of the formula V. In case of using a N-amino-N-2-hydroxyethyl-N '-fc phenyl substituted urea and aqueous formaldehyde, the process according to the invention can be represented by the following formula: The following cyclization to form the substituted 4- (phenylcarbamoyl) -tetrahydro-15 4 H-1, 3, 4-ox (or thia) diazine of the formula IV in the presence of acetic acid can be reproduced according to the process according to the invention through the following formula: 39 ^^^^^^^ »^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^ Instead of an acid, by way of example acetic acid, a metal oxide surfactant can also be used as the catalyst for the first step of the cyclization. • The last step of cyclization to form the ringed triazoles according to the invention, by using phosgene or another substituted 4 - (phenylcarbamoyl) - tetrahydro - 4 H - 1, 3, 4 - ox (or thia) diazine, can be reproduced through a following formula: The conversion of the N-amino-N'-phenylureas of the formula II 'with formaldehyde or paraformaldehyde is advantageously carried out in the presence of a solvent at temperatures in the range of 0-150 ° C, preferably d «10-100 ° C, Special preference is 20-60 ° C. As solvents, hydrocarbons such as pentane, hexane, heptane, cyclohexane, aromatic substances, for example benzene, toluene, xylene, heteroaromatic substances, for example pyridine, are used as solvents for these transformations, depending on the temperature range. , a, ß,? - picoline and quinoline, chlorinated hydrocarbons, for example methylene chloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, 1,1-dichloroethylene, • chlorobenzene, 1, 2 -, 1, 3 -, 1,4 - dichlorobenzene, 1 - chloronaphthalene and 1, 2, 4 - trichlorobenzene, ethers such as 1,4 - dioxane, anisole, glycol ethers such as dimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethyl ether, esters such as ethylacetate, propylacetate, methyl isobutyrate, isobutylacetate, carboxylic acid amides such as DMF, N-methylpyrrolidone, nitrohydrocarbons such as nitromethane, nitroethane, nitropropane and nitrobenzene, ureas as • tetraethylurea, tetrabutylurea, dimethylethyleneurea, dimethylpropyleneurea, sulfoxides as dimethyl sulfoxide, sulfones such as dimethylsulfone, diethylsulfone, tetramethylene sulfone, nitriles such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; water or also mixtures of isolated solvents. The molar ratios in which the starting compounds are converted to one another are generally 0.9-1.4, preferably 0.95-1.2, preferably 0.98-1.15 for the ratio of aldehyde to N-amino-N'-phenylurea of formula II '. The concentration of the effluents in the solvent is generally 0.1-5 mol / 1, preferably 0.2-2 mol / 1. Advantageously aqueous formaldehyde is added, preferably as a 37% solution during 2 to 20 minutes, to a mixture of the N-amino-N'-phenylurea of the formula II 'in one of the aforementioned solvents and then stirring to complete the reaction another 0.5 to 12 hours, preferably 1 to 3 hours at 20-60 ° C. 25 41 ^, ^ aifaijt-jc.

However, the N-amino-N'-phenylurea of the formula II 'can also be added to a mixture of formaldehyde in one of the aforementioned solvents and the reaction terminated as indicated above. ^^ In place of aqueous formaldehyde, paraformaldehyde can also be applied. The removal of reaction water is not usually required; In this case, the water of reaction can be separated by means of a water separator during the reaction. The reaction is carried out by excluding the acid catalysts, ie in? K a neutral to slightly alkaline medium. If necessary, the acid impurities are neutralized by adding basic compounds, for example alkali metal or alkaline earth metal hydroxides or hydrogenated carbonates or alkaline or alkaline earth metal carbonates. Eventually organic bases can also be added or work using a proportion of a basic solvent such as pyridine. The reaction can be carried out without pressure or under pressure in continuous or discontinuous fopna. Cyclization of the N-methyleneimino-N'-phenylureas of the formula III 'to form the 4 - (phenylcarbamoyl) - tetrahydro - 4 H - 1, 3, 4 - ox (or thia) diazines of the formula IV is by adding an acid of, generally, 1 to 100% by weight, with respect to formula III ', advantageously in the presence of one of the mentioned solvents, at temperatures within a range of 0-150 ° C, preferably of 10- 120 ° C, preferably special 20 - 80 ° C. As an acid, aromatic sulfonic acids can be used, Examples are benzenesulfonic acid, p-chloro-toluenesulfonic or p-toluenesulfonic acid, aliphatic sulphonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid and n-propylsulphonic acid, sulfamino acids such as methylsulfaminic acid, ethylsulfaminic acid or isopropylsulfaminic acid. , the aliphatic carboxylic acids such as acetic acid, trifluoroacetic acid, propionic acid, butyric acid or isobutyric acid, as well as inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid or boric acid. It is easy to use an acid such as acetic acid or propionic acid • directly as a means of reaction. Advantageously, N-methyleneimino-N'-phenylurea of the formula III 'is added for 2 to 20 minutes at 10-25 ° C to the organic acid, preferably acetic acid as the reaction medium, and stirring is continued for 0.5 to 12 hours. , preferably from 1 to 3 hours at 20-80 ° C. However, the acid can also be added directly to the reaction solution of the N-methyleneimino-N'-phenylurea step of the formula III 'formed of the N-amino-N'-phenylurea of the formula II 'and formaldehyde, and cyclization without isolation, as the case may be after the distillation of a part of the solvent, to form the 4- (phenylcarbamoyl) -tetrahydro-4H-1 , 3, 4-ox (or thia) 20 diazine of formula IV. The concentration of the effluents in the solvent is, in general, 0.1-5 mol / 1, preferably 0.2-2 mol / 1. Instead of an acid, a metal oxide surfactant can also be used as a catalyst. neutral or acid, as an example oxide of Aluminum, iron oxide, boron oxide, silicon dioxide, dioxide (eg titanium, arsenic oxide, antimony oxide, chromium oxide or manganese oxide.) The reaction can be carried out without pressure or under continuous pressure 0 discontinuous. Cyclization of the 4 - (phenylcarbamoyl) -tetrahydro-4 H-1,3,4-ox (or thia) diazines of the formula IV to form the compounds of the formula 1 is carried out by means of phosgene or a phosgene substitute, for example diphosgene (C1C (= O) 0CC13), advantageously in the presence of one of the abovementioned anhydrous solvents, at temperatures within a range of (-10) to 120 ° C, preferably from 0 to 80 ° C, preferably from 10 to 60 ° C.

Advantageously, the phosgene is introduced at 10-60 ° C under stirring in a mixture of a 4- (phenylcarbamoyl) -tetrahydro-4 H-1, 3, 4-ox (or thia) diazine of the formula IV and an amount of 0. , 5 - 5% by weight, with respect to formula IV, activated carbon as a catalyst in one of the above-mentioned anhydrous solvents for 0.5-20 hours, preferably 1-12 hours.

The reaction can be further accelerated by means of a basic amide catalyst, for example dimethylformamide, which can usually be applied in an amount of 0.3 to 10% by weight with respect to formula IV. Organic bases such as triethylamine, tri-n-propylamine, N, N-dimethylaniline or N, N-dimethylcyclohexylamine can also be used as the basic catalyst. Preferably, pyridine can also be used, if appropriate directly as a solvent. Instead of phosgene, diphosgene can be used. Advantageously, diphosgene is added for 2 to 20 minutes under stirring at 0 to (-5) ° C to the mixture of the starting material of the formula IV and one of the aforementioned solvents, if necessary by adding activated carbon, • dimethylformamide or an organic base, let it heat at 10 ° C for 1 hour and then stir for another 1-12 hours at 10-60 ° C. The molar amount of phosgene or diphosgene is 0.98 to 5, preferably 1 to 3, especially preferably 1 to 1.3 per mole of the starting material of formula IV. The concentration of the educts in the solvent is, in general, 0.1 f - 5 mol / 1, preferably 0.2 - 2 mol / 1. The reaction can be carried out without pressure or under continuous or discontinuous pressure . Advantageously, the reaction can be carried out in several stages as a single process, wherein in the first step of the synthesis in the After the conversion of the N-amino-N'-phenylureas of the formula II 'is eliminated with the reaction water, the N-methyleneimino-N'-phenylureas of the formula III' formed by cyclizing a neutral or acid catalyst to the 4 - • (phenylcarbamoyl) -tetrahydro-4 H -1,3,4-ox (or thia) diazines of the formula IV and then these are cyclized with phosgene or diphosgene if appropriate by adding activated carbon or an amide catalyst or in the presence of a base to the final products of formula I. Eventually the existing acid catalysts are separated by means of phase separation or distillation before phosgene cyclization, and then the ring closure is made to form the final substances of the formula I. For the preparation the intermediate products of the formula III '- IV are absorbed in a solvent not miscible with water, the acid or oxidizing impurities are extracted with alkali or diluted water, dried and the solvent is removed. at reduced pressure. Basically, the ring-shaped triazoles of the formula I can be prepared according to the above-mentioned synthesis method according to the invention. For economic reasons or for procedural techniques it may be more appropriate to prepare some compounds of the formula I from similar ring-shaped rings, but which differ in the meaning of a radical. The preparation of the reaction mixtures is generally carried out according to methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or extraction. of the solvent, or by elimination of the solvent, distribution of the residue in a mixture of water and a solvent organic and the preparation of the organic phase to form the product. The ringed triazoles of the formula I may contain one or more < centers of chirality and then enter as usual mixtures of enantiomers or diastereomers. If desired, the mixtures can be separated according to the usual methods for this, such as crystallization or chromatography, even in an optically active adsorbate, to form broadly pure isomers. Pure, optically active isomers can be prepared, by way of example, from the corresponding materials of optically active game. 46 Those triazoles ringed with R20 = OH, R22 and R25 = hydrogen can be transformed in a manner known per se into their salts, preferably tffc into their alkali metal salts. The salts of the formula F, whose metal ion is not an alkali metal ion, can be prepared in a customary manner by conversion to the sodium salt. corresponding alkali metal salt, likewise ammonium, phosphonium, sulfonium or sulfoxonium hydroxides. It is particularly advantageous to apply the process according to the invention to prepare the ringed triazoles of the formula I, wherein Q is • Q - 1 and R4 is a halogen atom, especially fluorine. These triazoles can to be accessed only with low yields according to the procedure described in WO 94/10173. Usually you get a mixture of different products difficult to separate. Another group of ringed triazoles that can be accessed well according to The process according to the invention is the new ringed triazoles of the formula I ', which represent another of the objects of the invention: where the variables have the following meanings: 25 47 Z O, S, S = O or S02; Halogen RA or C, -C 3 -alkyl; W1 oxygen or sulfur; R4 hydrogen or halogen; i i í ^ # R5 halogen, cyano or trifluoromethyl; R6 a group - C (R18) = C (R19) - CO - R20, - CH (R18) - CH (R19) - CO - R20, - C (R18) = C (R19) - CO - N (R20, R21), - CH (R18) - CH (R19) - CO - N (R20, R21), - C (R21) = N - OR22, - CO - OC (R23) (R24) - CO - OR '5, 15 CO - N (R26) - OR22 or C (OR27) = N - OR22; R18, R2 \ R24 in each case, hydrogen or C, -C, alkyl; R halogen, cyano or methyl; twenty R20 hydroxy, C, -C6-alkoxy, C3-C6-cycloalkoxy, C, -C4-alkoxy-C, -C4-alkoxy, Cl-C4-alkylthio-C, -C4-alkoxy, C, -C4-alkylsulfinyl- C, - C4 - alkoxy, C, - C4 - alkylsulfonyl - C, - C4 - alkoxy, cyano - C, - C6 - Alkoxy, C, -C 4 -alkoxycarbonyl-C, -C 4 -alkoxy, C 3 -C 6 -alkenyloxy, 48 C3 - C6 - alkynyloxy, C, - C6 - partially or fully halogenated alkoxy, C3 - C6 - partially or fully halogenated alkenyloxy, C3 - C6 - partially or fully halogenated alkynyloxy, C, - C6 - alkylthio, furthermore C, - C6 - alkoxy, which can carry two other substituents of C, -C6-alkoxy; R21 hydrogen, C, -C6 -alkyl or C, -C6 -halogenalkyl; R22 hydrogen, C, -C6 -alkyl, C, -C4 -alkoxy-C, -C4 -alkyl, C, -C6, f __? halogenalkyl, C, - C6 - cyanoalkyl, C3 - C6 - cycloalkyl, C3 - C6 alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6 haloalkynyl, carboxy-C, -C6-alkyl, C, -C6-alkoxycarbonyl C, -C4 -alkyl, C, -C6 -alkylcarbonyl-C , - C6-alkyl or C, -C6 alkylcarbonyloxy-C, -C6-alkyl; R25 hydrogen, C, -C6-alkyl, C3-C6-cycloalkyl, C, -C6-alkoxy-Cl-C4-alkyl, cyano-C, -C6-alkyl, halogen-C, -C6 -alkyl, C3- C6 • - alkenyl or C3-C6-alkynyl; R26, R27 independently of each other, C, -C6-alkyl, C, -C4-alkoxy-C, -C4-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C, - C6 - halogenalkyl, C, -C6-cyanoalkyl, C3-C6-halogenalkenyl, C3-C6-halogenalkynyl or C, -C6-alkoxycarbonyl-C, -C4-alkyl; 25 R: 26 in addition, hydrogen and • m 0, 1, 2 0 3, as well as the salts of the compounds of the formula I of utility in agriculture. With respect to the use of the ringed triazoles according to the invention as herbicides and / or as desiccant efficiency compounds / jStt , the substituents and the index m preferably have the following meanings, for themselves or in combination: Z oxygen; W1 oxygen; R5 chlorine or cyano, in spice] chlorine, R6 a group - C (R18) = C (R19) - CO - R20, - CH (R18) - CH (R19) - CO - 20 R20, - C (R21) = N - OR22, CO - OC (R23) (R24) - CO - OR25, CO - N (R26) - OR22 or C (O - R27) = N - OR22; R, R, R in each case, hydrogen or methyl; fifty R19 halogen or cyano; R20 C, - C6 - alkoxy, C3 - C5 - cycloalkoxy, C, - C4 - alkoxy - C, - C4 - alkoxy, • C, -C4-alkoxycarbonyl-C, -C4-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy or C, -C4-halogenalkoxy; > - R21 hydrogen or C, -C4-alkyl; R22 C, -C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6- • alkoxycarbonyl-C, -C2-alkyl; 10 R2S C, -C6-alkyl, C, -C6-C, -C4-alkyloxy, C3-C6-alkenyl or C3-C6-alkynyl; R26 hydrogen, C, -C6-alkyl, C, -C4-alkoxy-C, -C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6-alkoxy-carbonyl-C, -C2 - I rent; • R 27 C, -C 6 -alkyl, C, -C 4 -alkoxy-C, -C 4 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl or C, -C 6 -alkoxycarbonyl-C, -C 2 -alkyl; m zero The compounds of the formula I 'are listed in Table 1 (with W1 = oxygen and R5 = chlorine), in Table 2 the ringed triazoles of the formula I' 51 ^ H ^ r *** - !:. ^ -. ^ A. , ",. .% tA »í. > A¿.tffe-t. .. ^ fi »... with W "=: sulfur and R5 = chlorine: Table 1 Example Nr. R4 Z R6 Fuction Point • • (CDC13, d (1.01 H 0 -CH = N = OH. 1.02., FO -CH = N -OH 189-190 ° C 1.03 Cl 0 -CH = N-OH 204-207 ° C 1.04 H 0 -CH = N-OCH 3 166-168 ° C 1.05 F 0 -CH = N-OCH 3 173-175 ° C •) 53 54 ^^ ^^ Yes ^ iffi-i ^^^ .. • 15 twenty 40 Four. Five 55 ^^^ • • 57 i ^^^^ F ^^^ g ^^^^^^^^? Ffia ^ • • • • 59 * & ^^^^ ÉM 61 • 62 JJ ^^ W ^ ¿^ - - * i, g¡ & á > 3SS ¿S ?? * éÍL ?.

Continuation of table 1 • 15 • • 35 40 45 63 TABLE 2 64 tü "• Á." 'Then the ringed triazoles of formula I are also preferred with X - X = C - O or C - S, V = C = W2, W and W2 = oxygen, m = zero , Q = Q5 with Y = oxygen, R7, R8 = hydrogen and R9 = C, - C6 - alkoxy (= active substances of the formula I "with Z = oxygen or axufre), ie, for example, the compounds of the Table 3: 65 • Tabelle 3 66 ^ jijjAa &j The compounds of the formula I 'and their salts for use in sagriculture are suitable as herbicides - either as isomer mixtures or in the form of pure isomers. Herbicidal agents containing the • Compounds of formula F fight the growth of plants on non-cultivable surfaces very well, especially with large amounts of application. In crops such as wheat, rice, corn, soybeans and cotton they act against weeds and harmful grasses, without seriously damaging crops. This effect appears especially in case of scarce amounts of application. Depending on each application method, the • 10 compounds of the formula I 'or the herbicidal agents that contain them in a greater number of crops, in order to eliminate the unwanted plants. The following crops are counted among them, by way of example: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), W Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hiisutum, ( Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza Sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, 67 Jz aíaSf- T &? * Prunus pérsica, Pyrus communis, Ribes sylvestre, Ricinus comnunis, Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (see vulgare), Theobroma cacao, Trifolium pratense, aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays. In addition, the compounds of the formula F can also be applied in crops that are tolerant to the action of the herbicides, including the crops by genetic methods. The application of the mixtures and herbicidal agents according to the invention can be carried out in a process before or after emergence. If the active principles for certain crops are less tolerant, performance techniques can be applied in which the herbicidal agents are injected with the help of injectors so that the leaves of the sensitive crops do not touch each other as much as possible, while the substances active plants reach the leaves of the unwanted plants that grow below them or lbgan to the surface of the bare soil (post - directed, lay - by). The compounds of the formula F or the herbicidal agents containing them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also in the form of suspensions or dispersions of high aqueous, oily or other content, emulsions, dispersions in oil, pastes, dedusting agents, abrasives or granules by dusting, atomization, pulverization, disintegration or spillage. The forms of use are oriented according to the purposes of application; in each case they should guarantee as much as possible the most precise distribution of the active principles of the invention. Inert additives are essentially concerned: fractions of mineral oil with a medium to high boiling point, such as kerosene or diesel oil, as well as mineral tar oils, as well as oils of vegetable or animal origin, aliphatic hydrocarbons, cyclic and aromatic, for example paraffin, tetrahydronaphthalene, naphthalenes • alkyls or their derivatives, alkylated benzoles or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents such as, for example, amines such as N - methylpyrrolidone or water. The aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or ^ granules dispersible in water by addition of this. To prepare emulsions, pastes or dispersions in oil, the substrates can be homogenized in water as such or dissolved in an oil or in a solvent, by means of humectants, adhesives, dispersants or emulsifiers. But also from the active substance, the humectants, the adhesives, the dispersants or the emulsifiers and eventually the solvents or the oil, resistant concentrates can be prepared, which are suitable to be diluted with water. The alkali metal salts are taken into account as surfactants, • alkaline earth metal salts, ammonium salts of aromatic sulphonic acids, for example sulfonic acids of lignin, phenol, Naphthalene and dibutylnaphthalene, as well as fatty acids, alkylsulfonates and alkylaryl sulphonates, alkyl sulfates, lauryl ether sulfates, fatty acid sulfates, as well as the salts of hexadecanols, heptadecanols and sulfated octadecanols and the glycol ether of alcohol grease, sulfonated naphthalene condensation products and their derivatives with formaldehyde, condensation products of naphthalene or acids 69 g ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Isobutylphenol, octylphenol or nonylphenol ethoxylates, alkylphenyl polyethylether, tributylphenylpolyglycol ether, alkylarylpolyether alcohols, isotridecyl alcohol, ethylene oxide condensates of fatty alcohols, ethoxylated acid oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, polyglycol ether of lauryl alcohol, sorbitan ester , lignin residual liquors-sulphite or methylcellulose. Powders, abrasives and dedusting agents can be manufactured by mixing or grinding the active substances with a solid carrier. The granules, for example the granules for coating and impregnation and the homogeneous ones can be prepared by mixing the active substances with the solid carriers. Solid vehicles are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, calcium carbonate, lime, chalk, bolus alba, loess, clay, dolomite, earth of infusoria, calcium sulfate and magnesium sulfate, oxide of magnesium, crushed plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark flour, wood and nut husks, cellulose or other solid vehicles. The concentrations of the active ingredients of the formula F in the preparations to be applied can vary widely. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are applied in this case in a purity of 90% to 100%, preferably 95% to 100% (following the NMR spectrum). The compounds of the formula F can be formulated, by way of example, in the following manner: I. 20 parts by weight of compound No. la. 1.05 dissolve in a mixture • composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of 8 to 10 moles of ethylene oxide in 1 mol of N-monoethanolamide of oleic acid, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 mol of ethylene oxide in 1 mol of castor oil. With the pouring and fine distribution of the solution in ^ 100 000 parts by weight of water an aqueous dispersion is obtained which contains 0.02% by weight of the active substance.

II. 20 parts by weight of compound No. 1.23 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 15 moles of ethylene oxide in 1. mole of isooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide in 1 mole of castor oil. With the pouring and fine distribution of the solution in • 100 000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained. 20 III. 20 parts by weight of the active substance No. 1.79 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a melting point of 210 to 280 ° C and 10 parts by weight. parts by weight of the addition product of 40 moles of ethylene oxide in 1 mole of castor oil. With the spill • 38 ** rf? A «< «T ^ _. ^ & i. and the fine distribution of the solution in 100 000 parts by weight of water yields an aqueous dispersion containing 0.02% by weight of the active substance. fr IV. 20 parts by weight of the active substance No. 1.23 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of sodium salt of a lignin sulphonic acid obtained from a residual sulphite liquor and 60 parts by weight of silicic acid gel powder, and crushed in a hammer mill. With the fine distribution of the mixture in 20,000 parts by weight of water, a spray mixture containing 0.1% by weight of the active substance is obtained.

V. 3 parts by weight of active substance No. 1.05 are mixed with 97 parts by weight of micronized kaolin. In this way, a dedusting agent containing 3% by weight of the active substance is obtained.

SAW. 20 parts by weight of active substance No. 1.95 are mixed well with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol condensate - Urea formaldehyde and 68 parts by weight of a paraffinic mineral oil. A stable oil dispersion is obtained.

IL 1 part by weight of active substance No. 1.98 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight ^ "¿Weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. It can then be diluted with water to obtain the desired concentration of active principle. You get a concentrate • stable emulsion.

VIII. 1 part by weight of the active substance No. 1.02 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (= non-ionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.

In order to broaden the spectrum of action and to achieve synergistic effects, the ringed triazoles can be mixed and distributed in conjunction with numerous representatives of other groups of active herbicidal or growth regulating substances. By way of example, the agents 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, the amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, acids (het) - aryloxyalkanes and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1, 3-cyclohexandiones, heteroaryl - aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, -chloroacetanilides, cyclohexane-1,3-dionderivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halogencarboxylic acids and their derivatives, ureas, 3 - phenyluracils, imidazoles, imidazolinones, N - phenyl - 3, 4, 5, 6 - 2 tetrahydroftalimides, oxadiazoles, oxiranes, phenols, esters of aryloxyphenoxypropionic acid or the esters of heteroaryloxyphenoxypropionic acid, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils. Furthermore, it may be advantageous to distribute the compounds of the formula F alone or in combination with other herbicides or parasiticides, for example with agents for controlling parasites or phytopathogenic fungi or bacteria. It is also of interest the possibility of mixing them with • mineral salt solutions, which are applied to correct the deficiencies of food and trace elements. Non-phytotoxic oils and oily concentrates can also be added. The amounts of application of the active substance according to the combat purpose, the time of year, the target plants and the growth stage are from 0.001 to 3.0, preferably from 0.01 to 1.0 kg / ha of active substance. . Example 1 a) N-amino-N-2-hydroxyethyl-N '- (4-chloro-2-fluoro-5-methoxy iminomethyl-phenyl) urea 63.8 g (0.63 mol) of triethylamine were added at 0-5 ° C under stirring to a solution of 47.9 g (0.63 mol) of hydrazinoethanol in 300 ml of 1,2-dichloroethane and stirred for 30 minutes Then, 0.63 mol (100% stan) of 4-chloro-2-fluoro-5-methoxyimino were added at the same temperature. 74 ~ Zt-methyl-phenyl-isocyanate was 75% pure, suspended in 1,2-dichloroethane for 1 hour, and stirred for 12 hours. The precipitate that formed was removed and dried, yielding 20.6 g as a byproduct (14.7% of the • theoretical) of the corresponding substituted diphenylurea with a melting point of > 260 ° C. * 5 In the filtrate were left to concentrate by evaporation 211.6 g (88.2% of theory) of the crude title that appears in the title as a yellowish resin. 'H-NMR (en (CD3) 2 SO); d [ppm] = 3.95 (s / 3) CH30; 4.9 (s / 2) f NH2; 7.5 (d / 1) Ph; 8.3 (s / 1) CHO; 8.7 (d / 1) Ph; 9.1 (s / 1) NH. 10 b) N-Methyleneimino-N-2-hydroxyethyl-N '- (4-chloro-2-fluoromethoxyiminomethyl-phenyl) urea 27.6 g (0.34 mol) of a 37% formaldehyde solution is added under stirring at 22-25 ° C for 15 minutes to a solution of 90.2 g (0.296 mol) of the compound obtained in step a) in 700 ml of chloride • Methylene and stirred for 14 hours at 23 ° C. The aqueous phase was separated and the organic phase was stirred until dried over activated charcoal and magnesium sulfate. After removing on silica gel and concentrating by evaporation, 83.9 g (89.6% of theory) of the title compound having a melting point of 138-139 ° C were obtained. C) Tetrahydro - N - (4-Chloro-2-fluoro-5-methoxyimino-methyl-phenyl) -4 H -1,3,4-oxdiazin-4-carboxamide 22.5 g (0.072 mol) of the compound shown in the title, obtained in Step b) will be stirred in 350 ml of glacial acetic acid for 5 hours at 70 ° C gerührt. The clear reaction solution obtained was concentrated by evaporation, the residue was diluted with methylene chloride, washed with a sodium bicarbonate solution and dried. After extracting on silica gel, concentrating by evaporation and stirring with diisopropyl ether, after extraction and drying 9.7 g (42.6% of theory) of the compound in the title were obtained with a melting point of 169 - 171 ° C. d) 8 - (4'-chloro-2'-fluoro-5'-methoxyiminomethyl-phenyl) 4-oxa-7,9-dioxo-1, 2, 8-triaza [4.3.0.] Nonane (compound 1.05 from Table 1) 15 g (0.0475 mol) of the compound prepared in Step c) were transformed analogously to Example 4c with 9.4 g (0.0474 mol) of diphosgene in 200 ml of pyridine in the compound shown in the title. HE obtained 14.1 g (86.9% of theory) of it with a melting point of 173-175 ° C. Example 2 (comparison) 0.54 g (0.018 mol) of a 37% formaldehyde solution was added under stirring at 22 ° C to a solution of 5 g (0.0164 mol) of the compound obtained in Example la) and 0.5 g of p-toluenesulfonic acid in 250 ml of dichloromethane and stirred under reflux for 10 hours. The reaction mixture was concentrated by evaporation, the residue was dissolved in methylene chloride, purified with activated charcoal and extracted on silica gel. We obtained 2 fractions -0.3 g as resin that was composed, according to the spectrum 76 NMR mainly by aliphatic impurities, and 3.1 g as yellowish crystals with a melting point of 105-110 ° C, which consisted of 1 1 components according to the thin layer chromatographic examination. According to him • HPLC assay had produced at most 0.673 g of the le compound (a yield of 12.9%). (The NMR spectrum was so disparate that it could not be evaluated.) This shows that with the joint use of acid in the first stage the desired intermediate products can not be obtained with the necessary purity. Example 3 fa) N-amino-N-2-hydroxyethyl-N '- (4-chloro-2-fluoro-5-10 methoxy-phenyl) urea was obtained starting from 121 g (0.569 mol) of 4-chloro-2 - fluoro-5-methoxy-phenylisocyanate, analogously to Example la. 94.5 g (59.7% of theory) of the title compound having a melting point of 125 were isolated. fifteen - . 15 - 128 ° C. b) N-Methyleneimino-N-2-hydroxyethyl-N '- (4-chloro-2-fluoro-5-methoxy-phenyl) urea • 27.8 g (0.1 mol) of the compound obtained in step a) and 9 g (0.1 1 mol) of an aqueous solution 20 of 37% formaldehyde were placed in 500 ml of methylene chloride and stirred for 2 hours at 42 ° C. The reaction mixture was dried over magnesium sulfate and extracted on silica gel. After concentrating by evaporation, 25.6 g (84% of theory) of the title compound having a melting point of 141-142 ° C were obtained. 77 cl) Tetrahydro - N - (4 - chloro - 2 - fluoro - 5 - methoxy - phenyl) - 4 H - 1, 3, 4 - oxdiazin - 4 - carboxamide 19.2 g (0.0663 mol) of the product prepared in Step b) were stirred in 250 ml of glacial acetic acid for 2 hours at 60 ° C. The reaction mixture was concentrated by evaporation in vacuo and the residue was stirred in diisopropyl ether / pentane (2: 1). After extracting and drying, 11.5 g (59.9% of theory) of the compound in the title were obtained with a melting point of 147-150 ° C. The mother liquor was obtained by? K concentration by evaporation and by treatment as above, another 1.8 g (9.4% of theory) with a melting point of 145-147 ° C. c2) Tetrahydro - N - (2,4 - dichloro - 5 - methoxy - phenyl) - 4 H - 1, 3, 4 - oxdiazin - 4 - carboxamide (alternative to cl) A mixture of 29.4 g (0.1 mol) of N-amino-N-2-hydroxyethyl) - N ' - (2,4-dichloro-5-methoxy-phenyl) urea and 9 g (0.11 mol) of a 37% formaldehyde solution in 500 ml of methylene chloride were stirred for 2 hours at 42 ° C. After cooling, the reaction mixture was extracted on a pad with approx. 300 ml of silica gel and washed with methylene chloride. Here, the thin layer chromatographic assay resulted in a higher value relative to the reaction mixture not treated with silica gel, which remained in the methyleneimino stage. After concentrating by vacuum evaporation, 27.8 g (81.8% of theory) of the compound in the title were obtained with a melting point of 128-130 ° C. 78 ^ '&& amp; * ^ ". ? '.? ... í ^ M ^ &? ^ E ^ g to ^ - ^ Sg ÁÁ ssi ^ ^ Sae Example 4 a) N - amino - N - 2 - hydroxyethyl - N' - (2, 4 - dichloro - 5-methoxyiminomethyl-phenyl) urea was obtained starting from 166 g (0.6776 mol) of 2,4-dichloro-5-methoxyiminomethyl-phenylisocyanate analogously to Example la. After concentrating by evaporation and treating with solids, 74.6 g (34% of theory) of the title compound having a melting point of 152-156 ° C were isolated as a slightly soluble fraction. 75 g with a melting point of 168-200 ° C, which contained according to the NMR spectrum another 45 g (20% of theory) of the compound shown in the title. The difficu soluble fraction contained further, according to the NMR spectrum, N '- 2 - hydroxyethyl - N - (2, 4 - dichloro - 5 - methoxyiminomethyl - phenylcarbamoyl) hydrazide as a secondary component. b) Tetrahydro-N- (2,4-dichloro-5-methoxyimino-methyl-phenyl) -4 H 1, 3, 4-oxdiazin-4-carboxamide • A mixture of 53.5 g (0.1666 mol) of the compound obtained in the Stage a) and 14.9 g of a solution of formaldehyde at 37% in 1 1 of methylene chloride was stirred for 3 hours at 42 ° C. A sample gave, upon precipitation with pentane, extract, wash and dry, the corresponding intermediate stage of met'ilenimino with a melting point of 156 - 157 ° C? - NMR (en (CD3) 2 SO); d [ppm] = 9.3 (1 / s) NH; 8.4 (1 / s) = C-25 H; 7.8 (l / s) and 8.74 (l / s) Ar; 6.6 (l / d) and 7.05 (l / d) N = CH2; 4.8 (l / t) OH, 3.98 (3 / s) CH30; 3.5 (m / 2) and 3.95 (m / 2) CH2-CH2. The reaction mixture was mixed with 200 ml of acetic acid and stirred for 40 hours at 43 ° C. After cooling, the produced precipitate was extracted, washed with a little methylene chloride and dried. 23.3 g of the title compound were obtained with a melting point of 222-223 ° C. Another 13 g with a melting point of 205-208 ° C were isolated from the filtrate, so that the total yield amounted to 65% of the theoretical. Kc ^) 8 - (2 ', 4' - dichloro - 5 '- methoxyimino - methyl - phenyl) - 4 - oxa - 7,9 - dioxo - 1, 2, 8 - triaza [. 4.3.0] nonane (compound 1.06 of Table 1) 9.8 g (0.0495 mol) of diphosgene were added during 10 minutes under stirring at 0 to (-5) ° C to a solution of 15 g (0.045 mol) of the compound obtained in Step b) in 200 ml of pyridine. After stirring for 1 hour at 0-10 ° C and 12 hours under heating to 22 ° C, the reaction mixture was concentrated by evaporation, extracted into methylene chloride and washed twice? times with water and 1 N hydrochloric acid. After drying over magnesium sulfate, stirring over activated carbon and extracting on silica gel, the reaction mixture was concentrated by evaporation. 1 1.3 g (68% of theory) of the title compound having a melting point of 184-185 ° C was obtained. Example 5 (procedure) SO a) N-Methyleneimino-N-2-hydroxyethyl-N '- (4-chloro-2-fluoro-5-propargyloxy-phenyl) urea • 5 g (16.57 mmol) of N-amino-N-2-hydroxyethyl-N '- (4-chloro-2-fluoro-5-propargyloxy-phenyl) urea (yellow resin, prepared analogously to Example 1) and 1.5 g (18.23 mmol) of 37% formalin were placed in 250 ml of methylene chloride and stirred for 3 hours at 42 ° C. After cooling, the reaction mixture was mixed with 2 spoons of sulphate of magnesium. It was then chromatographed on 200 ml of silica gel. f Performance: 3.77 g (72.4% of theoretical) of the valuable products as yellow resin. ? - NMP (in (CD3) 2 SO); d [ppm] = 7.55 (d / 1 H), 7.95 (d / 1 H) Ph, 6.6 (d / l H), 7.0 (d / l H) N = CH2. b) Tetrahydro-N- (4-chloro-2-fluoro-5-propargyloxy-phenyl) -4 H-15 1,3,4-oxdiazin-4-carboxamide A solution of 4.9 g (15.62 mmol) of compound 5a in 100 ml of acetic acid was stirred for 24 hours at 60 ° C, after which the reaction mixture was allowed to cool and concentrated by evaporation in vacuo. The residue is Chromatography with methylene chloride: diethyl ester (2: 1) on silica gel. Chromatograph with methylene chloride, finally with acetic ester. Yield: 1.4 g (29% of theory) of the valuable product as a yellow resin. ? - NMR (en (CD3) 2 SO); d [ppm] = 8.6 (s / 1 H) NH; 8.1 (d / 1 H), 7.48 (d / 1 H) Ph, 5.92 (t / l H) OH; 4.85 (s / 2) OCH2; 4.6 - 4.25 (m / 2 H), 4.9- 3.6 (m / 4 H); 3.6 (s / 1 H) - C CH. ^ Example 6 (Comparison, procedure) ^^ Tetrahydro-N- (4-chloro-2-fluoro-5 -'-propargyloxy-phenyl) 4 H -1,3,4-ox-diazin-4-carboxamide 5.0 g (16.57 mmol) of the same material heading used in the Example 5a, 1.5 g (18.23 mmol) of 37% formalin and 0.5 g of p - acid. **, - toluenesulfonic were stirred in methylene chloride for 17 hours at 42 ° C? • in a water agitator. After cooling, the reaction mixture was partially concentrated by evaporation under vacuum. The purification was carried out by means of chromatography on 200 ml of silica gel (eluent, first methylene chloride, then methyl ester of acetic acid). Yield: 3.6 g of a mixture of substances, which was composed of 6 - 7 substances according to DC, HPLC and NMR. The HPLC assay had contained the title compound with 0.74 g (14.2% of theory). By rinsing the acid with methanol, only the p-toluenesulfonic acid could be isolated. Application examples The herbicidal action of the ringed triazoles of the formula F could be demonstrated by means of greenhouse tests with the compound of Example 1 (1.05 of Table 1): Plastic pots with muddy sand were served as containers for the crops with approx. . 3.0% humus as substrate. The seeds of the test plants were seeded separately according to type. For emergency pre-treatment the active ingredients 82"* ,. < > suspended in water or emulsified were applied directly after sowing by means of nozzles of exact distribution. The containers were lightly soaked to stimulate germination and growth, and • then covered with transparent plastic bells, until the plants grew. This coating results in a homogeneous germination of the 5 test plants as long as they are not damaged by the active ingredients. For the purpose of emergency after-treatment, the test plants grew first-depending on the type of growth-up to a height of ^ 3 to 15 cm, and only then were they treated with the active substances suspended? Or in water or emulsified. The test plants were seeded directly and placed in the same containers, or they were first grown separately as shoots and transplanted a few days later before treatment into the test vessels. The amount to be used for the subsequent emergency treatment was 0.0313 or 0.0156 kg / ha of active substance.

The plants were maintained according to the specific type at temperatures of 10-25 ° C or 20-35 ° C. The test period was extended for 2 to 4 weeks. During this time the plants were taken care of, and their reaction was evaluated • against each of the treatments. It was evaluated according to a scale from 0 to 100. Here, 100 means null appearance of plants, or else it means a total destruction of at least the aerial parts; and 0 means no damage or normal course of growth. The plants used in greenhouse trials are composed of the following types: 83 3 & j¿ - ^ ¡^ In the test of the compound of Example Id the following results were obtained: Example No. 7 8 C ant i d ad of 0.0313 0.0156 application (kg / ha s a.) Test plants ABUTH 100 100 CHEAL 98 98 GALAP 98 98 POLPE 98 98 SOLNI 100 100 VERSS 100 100 The results document the good herbicidal efficacy of the new ringed triazoles of formula F. 84 ^ ma ^

Claims

CLAIMS 1 -Procedure to prepare ring triazoles of formula I, where the substituents have the following meanings: • 10 X-X C-O, C-S, C-SO, C-S02 or C-N (R1); V C = W2, R'R2C - C (= W2) - or C (= W2) - C (= W2) 15 W1, W2 oxygen or sulfur; RA hydrogen, hydroxy, COOH, COOR2, halogen, cyano, C • (O) NRpR-2, OR3, C, -C6-alkyl, C, -C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, COR3, S (O) n R3 or 20 C (O) SR2; R1 hydrogen, hydroxy, halogen, CN, C, -C6-alkylo, C.-Cg-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, COR3, CHO, OR3, COOR2, C (O) SR2, C (O) NRpR12; Hydrogen R2, C, -C6-alkyl, C, -C6-haloalkyl, C2-C6 alkenyl or C2-C6-alkynyl; • R3 C, -C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C (-C6-haloalkyl, C, -C6 -alkoxy-C, -C6 -alkyl, carboxyl- C, -C6-alkyl, C, -C6-alkoxycarbonyl-C- C6-alkyl, C, -C6-alkylthio-C, -C6-alkyl, C, -C6-alkylsulfinyl-C, -C6-alkyl, C , C6-alkylsulfonyl-C, -C6-alkyl, C3-C6-cycloalkyl- • C, -C6-alkyl, C3-C6-alkenyloxycarbonyl-C, -C6-10 alkyl, C3-C6-alkynyloxycarbonyl-C, C6-alkyl, C3-C6-cycloalkoxy-C, -C6-alkyl, C3-C6-alkenyloxy-C, -C6-alkyl, C3-C6-alkynyloxy-C, -C6-alkyl, C, -C6-haloalkoxy- C, -C6-alkyl, C3-C6-15 haloalkenyloxy-C, -C6-alkyl, C3-C6-haloalkynyloxy-C, -C6-alkyl, C3-C6-cycloalkyl-C, -C6-thioalkyl, C3-C6 alkenylthio-C, -C6-alkyl, C3-C6-alkynylthio-C, -C6 -alkyl, cyano-C, -C6 -alkyl, C3-C6 -halocyclo-C, -C6 -alkyl, halogen- C3 twenty - . 20-C6-alkenyl, C, -C6-alkoxy-C3-C6-alkenyl, C, -C6-haloalkoxy-C3-C6-alkenyl, C, -C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl , C, - C6 - C3 - C6 alkynyl - alkynyl, C3 - C6 - haloalkoxyalkynyl, C, - C6 - alkylthioalkynyl, C, - C6 - alkylcarbonyl, CHRl6C0R17, 25 CHR16P (O) (OR, 7) 2, P (O) (OR17) 2, CHR, 6P (S) (OR17) 2, CHR16C (O) NR "R12, CHR16C (O) NH2, C , - C6 - alkyl, which is substituted by phenoxy or benzyloxy, where • the rings can be replaced by halogen, C, -C 4 -alkyl or C, -C 4 -haloalkyl, benzyl which can be substituted by halogen, C, -C-alkyl or C, -C 4 -haloalkyl or phenyl and pyridyl , which can be substituted by halogen, C, - C - alkyl, C, - C4 - haloalkyl or C, - C4 - alkoxy; 10 m the value 0, 1, 2 or 3; n the value 0, 1 or 2; one of the radicals Q - 1 to Q - 7 15 • twenty 25 87 -TO. ..t fifteen • twenty with And oxygen or azure; R4 hydrogen or halogen; R5 C, -C6-alkyl, C, -C6-haloalkyl, OCH3, SCH3, OCHF2, halogen, CN or N02; • R6 hydrogen, C, -C6-alkyl, C, -6-haloalkyl, halogen, OR10, S (O) nR10, COR10", COOR10, C (O) SR10, SCH2C to CH, C (O) NRUR12, CHO, CH = CHCO - OR10, CO - ON = CR13R14, NO CN, NHS02R15, NHS02NHR15, - C (R18) = C (R19) - CO - R20, - CH (R18) - CH (R19) - CO - R20 , - C (R18) = C (R19) - CO - N (R20, R21), - CH (R18) - CH (R19) - CO - N (R20, R21), - C (R21) = N - OR22 , - 10 COOC (R23) (R24) - COOR25, - CO - N (R26) - OR22 or - C (OR27) = N - OR22; R7, R8 independently of one another, hydrogen, C, -C6-alkyl, 15 C, -C6 -haloalkyl or halogen; when Q is Q-2, Q-5 or Q-6, R7 and R8 can form, together with the carbon atom to which they are attached, a C = O group; • R9 C, - C6 - alkyl, C, - C6 - haloalkyl, C, - C6 - alkoxy, C, 2o-C6-C6-C6-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl alkoxy; R10 one of the radicals indicated in R3; R ", R13 independently of one another, hydrogen or C, -C6-alkyl; R 12, R 14 independently of one another, C, -C 6 -alkyl or phenyl, which f, can be substituted by halogen, C, -C 4 -alkyl, C, -C 4 -haloalkyl or C, -C 4 -alkoxy; R "and R12 can together be a group - (CH2) 5 -, - (CH2) 4 - or - ~ CH2CH2OCH2CH2 -, where each ring can be R13 and R14 can also form, together with the carbon atom to which they are attached, a C3-C8-cycloalkyl group; R 15 C, -C 6 -alkyl or C, -C 6 -haloalkyl; fifteen R16 hydrogen or C, -C6-alkyl; R17 C, -C6 -alkyl, C2-C6-alkenyl or C2-C6-alkynyl; R18, R23, R24 in each case, hydrogen or C, -C3-alkyl; R19 halogen, cyano or methyl; 25 R20 hydroxy, C, - C6 - alkoxy, C3 - C6 - cycloalkoxy, C ^ - C - 90 -. 90- ^^? Sa-S-^? Aa¡a¿- »g¿ ^ C4-alkoxy-alkoxy, C, -C4-alkylthio-C, -C4-alkoxy, C, -C4-alkylsulfinyl- C, - C4 - alkoxy, C, - C4 - alkylsulfonyl - C, - C4 - alkoxy, cyano - C, - C6 - alkoxy, C, • - C4 - alkoxycarbonyl - C, - C4 - alkoxy, C3 - C6 - alkenyloxy, C3 - C6 - alkynyloxy, C, - C6 - partial alkoxy 5 or fully halogenated, C3 - C6 - partially or fully halogenated alkenyloxy, C3 - C6 - partially or fully halogenated alkynyloxy, C, - C6 - alkylthio, in addition C, - C6 - alkoxy which can carry two other substituents of C, - C6 f 10"alkoxy > R21 hydrogen, C, -C6 -alkyl or C, -C6 -halogenalkyl; R22 hydrogen, C, -C6-alkyl, C, -C4-alkoxy-C, -C4-15 alkyl, C, -C6-halogenalkyl, C, -C6-cyanoalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl , C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, • carboxy - C, - C6 - alkyl, C. - C6 - alkoxycarbonyl - C, - C4 - alkyl, C, - C6 - alkylcarbonyl - C, - C6 - alkyl or C, 20-C6-alkylcarbonyloxy-C, -C6-alkyl; R25 hydrogen, C, -C6 -alkyl, C3-C6-cycloalkyl, C, -C6 -alkoxy-C, -C4 -alkyl, cyano-C, -C6 -alkyl, halogen-C, -C6 -alkyl, C3- C6-alkenyl or C3-C6-alkynyl; R26, R27 independently of each other, C, -C6-alkyl, C, -C4-alkoxy-C, -C4-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C, - C6 - halogenalkyl, C, - F C6 - cyanoalkyl, C3 - C6 - halogenalkenyl, C3 - 06 - halogenalkynyl or C, - C6 - alkoxycarbonyl - C, - C4 - alkyl; R26 in addition, hydrogen, characterized in that compounds of formula II are converted in a first step. 15 with formaldehyde or aqueous paraformaldehyde in the presence of acids in a neutral or slightly alkaline medium to form N-methyleneimino-N'-substituted ureas of formula III 25 because they are cyclized in the presence of catalytic amounts of acid or a neutral or acidic surfactant metal oxide to form tetrahydro-4 H-1, 3, 4-ox (or thia) substituted diazines of formula IV (RA) m and in that the latter are cyclized with phosgene, thiophosgene or a phosgene substitute to form the compounds of formula I.
2. - Process according to claim 1, characterized in that the cyclization of the compounds of formula III to form the tetrahydro-4 H -1, 3, 4-ox (or thia) substituted diazines of formula IV is carried out in the presence of a metal oxide surfactant . 3. Method according to claim 2, characterized in that silica gel is used as the metal oxide surfactant. 4. Triazoles ringed according to claim 1, characterized in that they have the formula F where the variables have the following meaning: Z O, S, S = O or S02; • Halogen RA or C, -C 3 -alkyl; R4 hydrogen or halogen; R5 halogen, cyano or trifluoromethyl and • R 6 a group - C (R 18) = C (R 19) - CO - R 20, - CH (R 18) - CH (R 19) - CO - R 20, - C (R 18) = C (R 19) - CO - N (R 20) , R21), - CH (R18) - CH (R19) - C = O - N (R20, R21), - C (R21) = N - O - R22, - CO - OC (R23) (R24) - CO - O - R25, CO - N (R26) - OR27 or C (O - R27) = N 15 - OR22; R18, R2j, R24 in each case, hydrogen or C, -C3-alkyl; R19 halogen, cyano or methyl; twenty R20 hydroxy, C, -C6-alkoxy, C3-C6-cycloalkoxy, C, -C4-C, -C4 alkoxy-alkoxy, C, -C4-alkylthio-C, -C4-alkoxy, Ci-C4 alkylsulfinyl-C, - C4 - alkoxy, C, - C4 - alkylsulfonyl - C, - C4 Alkoxy, cyano-C, -C6-alkoxy, C, -C4-alkoxycarbonyl-C, -C4 94 j * ^ to «* g @ alkoxy, C3 - C6 - alkenyloxy, C3 - C6 - alkynyloxy, C, - C6 - partially or fully halogenated alkoxy, C3 - C6 - partially or fully halogenated alkenyloxy, C3 - C6 - partial alkynyloxy or totally • halogenated, C, -C 6 -alkylthio, in addition C, -C 6 -alkoxy, which can carry two other substituents of C, -C 6 -alkoxy, R21 hydrogen, C, -C6 -alkyl or C, -C6 -halogenalkyl; R22 hydrogen, C, -C6 -alkyl, C, -C4 -alkoxy-C, -C4 -alkyl, C.f.10-C6 -halogenalkyl, C, -C6-cyanoalkyl, C3-C6-cycloalkyl, C3-C6- alkenyl, C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-halogenalkynyl, carboxy-C, -C6-alkyl, C, -C6-alkoxycarbonyl-Ci-C4-alkyl, C.-C6-alkylcarbonyl-C , - C6 - alkyl or C. - C6 - alkylcarbonyloxy - C, fifteen - . 15-C6-alkyl; R25 hydrogen, C, - C6 - alkyl, C3 - C6 - cycloalkyl, C, - C6 • C4-C4-alkoxy, cyano-C, -6-alkyl, halogen-C, C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl alkoxy; twenty R26, R27 independently of each other, C, -C6-alkyl, C, -C4-C4-alkoxy-C4-alkyl, C3-C6-cycloalkyl, C3-C6 alkenyl, C3-C6-alkynyl, C, -C6-haloalkyl , C, C6 - cyanoalkyl, C3 - C6 - halogenalkenyl, C3 - C6 Halogenalkynyl or C, -C 6 -alkoxycarbonyl-C, -C 4 -alkyl; R26 in addition, hydrogen and m 0, 1, 2 0 3, as well as the salts of the compounds of formula I of utility in agriculture. 5.- Triazoles ringed with formula F according to claim 4,? characterized because the substituents and the index m have the following meanings: Z oxygen; R5 chloro or cyano; And a link, «fi R18, R23, R24 in each case, hydrogen or methyl; R19 halogen or cyano; R20 C, - C6 - alkoxy, C3 - C5 - cycloalkoxy, C ^ C ^ alkoxy - C, - C4 alkoxy, C, - C4 - alkoxycarbonyl - C, - C4 - alkoxy, C3 - C6 96 alkenyloxy, C3-C6-alkynyloxy or C, -C4-halogenalkoxy; R21 hydrogen or C, -C4-alkyl; • R22 C, -C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6-alkoxycarbonyl-C, -C2-alkyl; R2S C, -C6-alkyl, C, -C6-alkoxy-C, -C4-alkyl, C3-C6 • alkenyl or C3-C6 alkynyl; • R26 hydrogen, C, -C6-alkyl, C, -C4-alkoxy-C, -C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6-alkoxy-carbonyl-C | - C2 - alkyl; R27 C, -C6 -alkyl, C, -C4 -alkoxy-C, -C4 -alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6 -alkoxycarbonyl-C, -C2 -alkyl; • m 0, 20 as well as its useful salts in agriculture. 6.- N-substituted methyleneimino-N '-phenylureas useful as intermediates in the process according to claim 1, characterized in that they have the formula IIF 97 '& . , -, - = & - where the substituents have the following meanings: O, S, S = O or SO 2.
3 Halogen RA or C, -C 3 -alkyl; m 0, 1 or 2; W1 oxygen or sulfur; R4 hydrogen or halogen; R5 halogen, cyano or trifluoromethyl; R6 a group - C (R18) = C (R19) - CO - R20, - CH (R18) - CH (R19) - CO - R20, - C (R18) = C (R19) - CO - N (R20, R21), - CH (R18) - CH (R19) - CO - N (R20, R21), - C (R21) = N - OR22, - CO - OC (R23) (R24) - CO - OR25, CO - N (R26) - OR22 or C (O - R27) = N - OR22; 98 R, R, R2 in each case, hydrogen or C, -C 3 -alkyl; # R19 halogen, cyano or methyl; R20 hydroxy, C.-C6-alkoxy, C3-C6-cycloalkoxy, C, -C4-alkoxy-C, -C4-alkoxy, C, -C4-alkylthio-C, -C4-alkoxy, C, -C4-alkylsulfinyl - C, - C4 - alkoxy, C, - C4 - alkylsulfonyl - C - C4 - alkoxy, cyano - C, - C6 - alkoxy, C, - C4 - alkoxycarbonyl - C, - C4 - f alkoxy, C3 - C6 - alkenyloxy, C3-C6-alkynyloxy, C, -C6-partially or fully halogenated alkoxy, C3-C6-partially or fully halogenated alkenyloxy, C3-C6-partially or fully halogenated alkynyloxy, C, -C6-alkylthio, further Ci, - C6 - alkoxy, which can carry two other substituents of C, -C6-alkoxy; fifteen R21 hydrogen, C, -C6 -alkyl or C, -C6 -halogenalkyl; • R22 hydrogen, C, - C6 - alkyl, C, - C4 - C - C4 - alkoxy - alkyl, C - C6 - halogenalkyl, C, - C6 - cyanoalkyl, C3 - C6 - 20 cycloalkyl, C3 - C6 - alkenyl , C3-C6-alkynyl, C3-C6-haloalkenyl, C3-C6-haloalkynyl, carboxy-C, -C6 -alkyl, C, -C6-alkoxycarbonyl-C, -C4 -alkyl, C, -C6 -alkylcarbonyl-C , - C6 - alkyl or C, -C6-alkylcarbonyloxy-C, 25 -. 25-C6-alkyl; R25 hydrogen, C, -C6-alkyl, C3-C6-cycloalkyl, Ci-C6-C4-alkoxy-alkyl, cyano-C, -6-alkyl, halogen-C, -C6-alkyl, C3-C6 - alkenyl or C3-C6-alkynyl; R26, R27 independently of one another, C, -C6 -alkyl, C, -C4 -alkoxy-C, -C4 -alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C, -C6 - halogenalkyl, C, -C 6 -cyanoalkyl, C 3 -C 6 -halogenalkenyl, C 3 -C 6 -halogenalkynyl or C, -C 6 -alkoxycarbonyl-C, -C 4 - • alkyl, and R26 in addition to it, hydrogen. 7. Substituted N-methyleneimino-N '-phenylureas of formula III' according to claim 6, characterized in that the substituents have the following meanings: Z oxygen; R5 chloro or cyano; R, R, R24 in each case, hydrogen or methyl; R19 halogen or cyano; 100 R20 C, -C6-alkoxy, C3-C5-cycloalkoxy, C, -C4-alkoxy-C, -C4-alkoxy, C, -C4-alkoxycarbonyl-C, -C4-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy or C, -C4-halogenalkoxy; R21 hydrogen or C, -C4-alkyl; R22 C, -C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6-alkoxycarbonyl-C, -C2-alkyl; F 10 R 25 C, - C 6 - alkyl, C, - - C 1 - C 4 - alkoxy, C 3 - C 6 - alkenyl or C 3 - C 6 alkynyl; i \ R 26 hydrogen, C, -C 6 -alkyl, C, -C 4 -alkoxy-C, -C 4 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl or C, -C 6 -alkoxycarbonyl-15 C, -C 2 - I rent; _) R27 C, -C6-alkyl, C, -C4-C, -C4-alkoxy, C3-C6-alkenyl, C3-C6-alkynyl or C, -C6-alkoxycarbonyl-C, -C2-alkyl; twenty m zero 8 - Use of the ringed triazoles of formula F and the agricultural salts of formula F according to claim 4, characterized in that they are 25 101 useful as herbicides or for drying and / or defoliation of plants. 9.- Herbicidal agent characterized in that it contains an amount of herbicidal efficacy of at least one ringed triazole of formula F or of a salt of agricultural use of formula F according to claim 4, and at least f a liquid and / or solid inert carrier, as well as if desired at least one adjuvant 10. Agent for drying and / or defoling plants, characterized in that it contains an amount of desiccant and / or defoliant efficacy of at least one ringed triazole of formula F or of one of the salts of Formula F of utility in agriculture according to claim 4, and at least one liquid inert carrier a? and / or solid, as well as if at least one adjuvant is desired. 1. Procedure for combating the unwanted growth of plants, characterized in that a quantity of herbicidal effectiveness of at least one ringed triazole of formula F or a salt of formula F of use in agriculture according to claim 4 on plants, its habitat or in seeds. 12. Process for desiccating and / or defoling plants, characterized in that an amount of herbicidal efficacy of at least one ringed triazole of formula F or a salt of formula F of agricultural utility according to claim 4 is allowed to act on plants. - Ringed triazoles according to claim 1, characterized in that they have the formula I " 102 lafadaÉife, SUMMARY OF THE INVENTION A process for preparing ringed triazoles of formula I is described, where, first, the substituted N-aminoureas are transformed with formaldehyde or paraformaldehyde to form the corresponding methyleneimino derivatives, then cyclized in the presence of catalytic amounts of acid or in the presence of a metal oxide to form tetrahydro-4 H-1, 3, 4-ox (or thia) diazines and, finally, triazoles ringed with phosgene or a phosgene substitute are prepared. 10 (R vAep I N-Q x w1 The new ringed triazoles obtained according to the process according to the invention and the synthesis intermediates are also claimed. Finally, the use of said compounds as herbicides or for the desiccation and / or defoliation of plants and herbicidal agents and for drying and / or defoling plants, as well as the methods of 20 application of said compound L- 25 104 (C, -C6-alkoxy) wherein R4 is hydrogen or halogen. 10 fifteen twenty 25 103 KffSISti- '*? «M2S | Wß) í?