CA1082702A - 2,1,3-benzothiadiazin-(4)-one-2,2-dioxide derivatives - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE: New and valuable substituted 2,1,3-benzothiadiazin-(4)-one-2,2-dioxides having a herbicidal action and a process for controlling the growth of unwanted plants with these compounds.

Description

10~'713,.
The present inventio11 relates to new and valuable substituted ~,1,3-benzothiadiazin-(4)-one-2,2-dioxides having a herbicidal action, herbicides containing these active ingredients, a process for controlling the growth of unwanted plants with these compounds, and a method of manufactuting them.
It is known (German 1,542,836) that 3-isopropyl~2,1,3-benzothiadiazin-(4)-one-2,2-dioxide is used as a herbicidal active ingredient. However, it causes damage to crop plants.
We have now found that compounds of the formula R 1 - N~ ( XX~ ) R~

Where Rl denotes isopropyl and R2 denotes a) formyl, propionyl, valeryl, sec-valeryl, capronyl, l-(~-methylvaleryl), acyl of 8 to 16 carbon atoms, lower acyl substituted by halogen, acetoxy or alkoxy, lower acyl substituted by halophenoxy and/or alkylphenoxy, unsaturated unsubstituted acyl of 3 to 5 carbon atoms, cycloacyl of 6 to 10 carbon atoms, diacyl of 2 to 10 carbon atoms, or b) alkoxy- or alkylmercaptocarbonyl containing alkyl of 1 to ~ 16 carbon atoms in the alkoxy group, unsubstituted or ; a~xy-substituted phenoxycarbonyl, unsubstituted or halogen-substituted benzylmercaptocarbonyl, or c) unsubstituted or alkoxy-substituted dialkylcarbamoyl, dialkylthiocarbamoyl, N-phenyl-N', N'-dialkylformamidinyl, the alkyl group containing 1 to 5 carbon atoms, or d) alkylsulfonyl, containing 1 to 5 carbon atoms in the alkyl group, arylsulfonyl which may be substituted by halogen, nitro or alkyl of 1 to 5 carbon atoms, or ~ .
~. , -- 1 -- 7~
. . ..

lVti;~70~ ' e) mono- or dialkylsulfamoyl containing 1 to 5 car~on atoms ' in the alkyl group, or f) N-alkylbenzimidyl containing 1 to S carbon atoms in the alkyl group, or g) 0,0-dial~ylphosphorothioate or phosphate containing 1 to 5 carbon atoms in the alkyl group, or h) unsubstituted or perchloromethylthio, or -i) phenyl substituted by nitro, have a better herbicidal action than the prior art compound.
Examples of meanings for R are formyl, propionyl, n-butyryl, valeryl, isovaleryl, sec-valeryl, capronyl, oC -methyl-valeryl, enanthyl, pelargonyl, caprynyl, undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl, pentadecanoyl, palmitoyl, acetoxy-acetyl, chloroacetyl, dichloroacetyl, oc -chloropropionyl,oC,c~-dichloropropionyl, ~-chlorobutyryl, o~-chlorovaleryl, c~-chloro- ~ ' capronyl, ~-chloropropionyl, ir-bromobutyryl, acryloyl, but-(2)-enoyl-l, pent-(3-)-enoyl-1, methoxyacetyl, ~ -methoxy- ' propionyl, ~-methoxybu'cyryl, cyclopentanoyl, cyclohexanoyl, benzoyl, ~-naphthoyl, o-, m-, p-bromobenzoyl, o-, m-, p-nitro-benzoyl, phenoxyacetyl, p-chlorophenoxyacetyl, 2,4-dichloro-phenoxyacetyl, 2,4,5-trichlorophenoxyace'cyl, 2-methyl-4-chloro-phenoxyacetyl, 2,4-dichlorophenoxy-~-propionyl, oxalyl, malonyl, succinyl, glutaryl, adipoyl, decane-(1,10)-dioyl, C-bromo-butyryl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, iso-butoxycarbonyl, sec-butcxycarbonyl, n-pentyloxycarbonyl, . :

. . .

. ' ' ' .

7~

OOZ. 30,824 pentyl-(3) oxycarbonyl, cyclopentyloxycarbonyl, n-hexyloxy-carbonyl9 cyclohexyloxycarbonyl~ n-heptyloxycarbonyl, n octyl-oxycarbonyl~ n-nonyloxycarbonyl, n-deeyloxycarbonyl, undecyl-oxycarbonyl, dodecyloxycarbonyl, tridecyloxycarbonylJ tetra-decyloxycarbonyl, pentadecyloxycarbonyl, hexadecyloxycarbQnyl, o-methoxyphenoxycarbonyl, methylmercaptocarbonyl, ethyl~
mercaptocarbonyl, n-propylmercaptocarbonyl, lsopropylmercapto-carbonyl, n-butylmercaptocarbonyl, p-chlorobenzylmercapto~ar-bonyl, phenylmercaptocarbonyl, p~methoxyphenylmercaptocarbonyl, dimethylcarbamoyl, diethylcarbamoyl9 di-n~propylcarbamoyl, dlisopropylcarbamoyl, di-n-butylcarbamoylj di~sec-butyl-carbamoyl, N-methyl N-propoxymethylcarbamoyl, 1-plperidinoyl-, hexahydro-1~-H-azepln-1'-oyl, dlmethylthlocarbamoyl, diethyl-thiocarbamoyl, dl-n~propylthlocarbamoyl, dilsopropylthlo carbamoyl, N-phenyl-~N-dlmethyl~ormamldlnyl, methylsulfonyl, ethyl~ulfonyl, n-propylsulronyl, ~sopropylsulfonylJ n-butyl-sulronyl, isobu~ylsulronyl~ sec-butylsulronyl, n-pentyl-sul~onyl, benzenesulronyl, p-toluenesulronyl, o-, m-, p-bromo-benzenesulronyl, o-, m-, p-nltrobenzenesulronyl, B-naphthalene-: 20 sul~onyl, dimethylsulramoyl, dlethylsulfamoyl, di-n-propyl-sulramoyl, methylaminosul~onyl, ethylaminosulfonyl, n-propyl-amlnosul~onyl, lsopropylamlnosulfonyl9 n butylaminosul~onyl, N-methylbenzim~dyl, N-ethylbenzimidyl, N-propylbenzlmldyl, ; 0,0-dimethylphosphorothioate, 0,0-diethylphosphorothioate, 0,0-di-n-propylphosph~rothioateJ 0,0-dlmethylphosphate, 0,0-;
diethylphosphate9 perchloromethylth~o-2,4,6-trinltrophenyl.
The compounds o~ the rormula XXV in whlch R2 denotes substituted acyl or aroyl may be prepared for lnstance by ~; reactlng a l-alkall metal (or alkaline earth metal) or - 3 ~
, .' , ,,: ,":

0 ~ ~ 7 ~
O.Z. 30,824 ammonium salt of 3-lsopropyl-2,1,~-benzothladiazln-(4)-one-: 2,2-dloxide of the rormula II wlth a substltuted acyl hallde I
ln a polar solventJ in a temperature range o~ ~rom -10 to ~110C over a period of ~0 mlnutes to 12 hours:

R-0-Nal + ~ Nl ~ - MeHa1 25 Me O~C-R
I II IV
Me denoting an equivalent Or an alkall metal, alkaline earth metal or ammonlum lon, Hal denoting chloro or bromo, R-C0- `!
havlng the meanlngs given above under a) for R2 and ~ -denotlng i~opropyl.
Any metal or ammonlum salt whlch may have precipltated out 18 separated and the filtrate conoentrated tn vacuo.
Puri~lcation is e~ected by recrystallizatlon or by extractlon I with dilute alkali and wa~hlng until neutral with water-.
; immisclble solvents, In the latter case the compounds N
, , lsolated arter drying and oon¢entration o~ the organlc phase are pure.
i However, lt ls also possible to re~ct, in place Or startlng material II, the substance Or the ~ormula III whi¢h forms it, the reaetion taking pla~e under the above conditions in the ~resen¢e o~ a tertiary base:

R-C-Hal ~ t N ~ ~ N ~ J
i-~, 02~`N ~ HHal 02S~N
~ H 0=C-R
`1 I III IV
-:1 Hal denoting chloro or bromo and R-C0- having the meanlngs ~:l - 4 -. ~

.

,--.
i :

','V;~
o.æ. 30~8~4 given above under a) rOr R2.
Puri~icatlon ls efrected in conventlonal manner by ; extractlon o~ the water-soluble base hydrochlorlde and lsolation by the above procedure.
l-Pormyl-3-isopropyl-2,1,3-benzothiadlazln-(4)-one-2,2-dioxide (VI) is syntheælzed by reacting starting material III
with a mlxture o~ ~ormlc and acetic anhydrldes tV) and workln~
up as abo~e:

HC-0-C-CH3 + ~ N

H 0=C-~
V III ~I
If 2 equlvalents of the l-sodium salt of ~-lsopropyl-

2,1,3-benzothladlazin-(4)-one-2,2-dioxide (II) are reacted with 1 equivalent o~ oxalyl chlorlde VII as the slmplest representative oP low diacyl halides under the above reaction conditlons, the compound ha~lng the Pormula VIII is obtai~ed: .
~$~+Cl-C-CO-cl r~Jl . 2 , 2 .l Na _ C,Q 2 II VII VIII
To prepare substltuted l-alkoxy- or aryloxycarbonyl or .~ alkylmerca~tocarbonyl-~-iso~ropyl-2,1,~-benzothiadiazin-(4)-one-2,2-dioxldes (X), the ætarting salts of the formula II are reacted under the a~ove reaction conditions wlth appropriately . substituted ¢hloroPormates (IX), Me denoting an ~uivalent oP
an alkali metal, alkallne earth metal or ammonlum ion and .
: :

: , . ~. ' o.z. 30,824 -CO-OR or -CO-SR havlng the meanings glven aboYe under b) ~or R :

+Cl-C-OR I ~ ,, Me O--C-OR
SR ~ -II IX X
Simllarly, compounds XII are obtalned by reaction o~
compounds II wlth optionally substltuted dlalkylcarbamoyl or dialkylthlooarbamoyl chlorides or N-phenyl-N~,N'-dialkyl chloro~ormamldlnes XI; ln the ~ollowing scheme Me denotes an equlvalent o~ an alkali metal, alkaline earth metal or ammonium ion and O(S) (N-phenyl) has the meanings glven above under c) -C-NAlk2 10 rOr R2:
O (S); (N-phenyl) ~, ~ N ~ + Cl-C-NAlk2 , 02~`N~ 02S ~
Me (phenyl-N); (S);O=C-NAlk2 II XI XII
Compounds o~ the rormula XIV are simllarly obtained by reaction o~ optionally substltuted alkyl- or aryl~ulfonyl chlorides XIII with startlng compounds II; in the ~ollowlng scheme Me denotes an e~uivalent Or an alkali metal, alkallne earth metal or ammonium lon and -SO2R has the meanlng~ given : above under d) rOr R2:

~2 ~ + Cl-SO2-~
Me SO2R
; II XIII XIV
''~

'7V~' OOZ~ ~0,824 I~ mono- or dialkylsulramoyl chlorides X~ are used, compounds XVI are obtalned ln the manner described above, in the ~ollowing scheme Me denotes an equivalent o~ an ~lkall metal, alkallne earth metal or ammonlum lon and -S02-NAlk -NHAlK
has the meanln~s given above under e) for R'-O O

~q + cl-sO2-NAlk2 ~ >~
02S~ ~ -NHAlk 02S~N,~
Me ~02-NAlk2 -NHAlk II XV XVI
Ir N-alkylbenzlmlde chlorldes XVII are analogously reacted with starting salts II, l-(N-alkylbenzimidyl)-3-lso-propyl-2,1,3-benzothiadiazln-(4)-one-2,2-dioxldes o~ the ~ormula XVIII are obtained; ln the followlng scheme Me denotes an equlvalent o~ an alkall metal, alkaline earth metal or ammonlum ion and -C=N-Alk has the meanings given above under i~ ) ror R2: ¢~

O O
02S~ + ~3C_N-Alk Me ~ C=N-Alk Il XVII XVIII ~ ;
Ir optionally halo~enated alkylsul~enyl halldes XIX are used, l-alkylthio-~-isopropyl-2,1,3-benzothiadlazln-t4)-one 2,2-dioxldes XX are obtalned; in the ~ollowlng s~heme Me denotes an equivalent of an al~ali metal9 alkaline earth metal :
or ammonlum ion and -SR has the meanings given above under h) ~;

. . . - . .

~'~7V~
O O Z~ ~OJ 824 ~or R2:
O O
1~ +C1SR ~~ C
>_N ~ ~--N~

02S~ , ; Me S-R
II XIX XX
Ir starting salts II are slmllarly reacted wlth a dialkylphosphoric ester hallde XXI, 3-lsopropyl-2,1,3-benzo-thladiazln-(4)-one-2,2 dioxide-l-(O,O-dialkylphosphoro-thioates or phosphates) XXII are obtained; ~n the rollowlng scheme Me denotes an equivalent Or an alkall metal, alkallne earth metal or ammonium ion and -P3(0Alk)2 has the meanlngs glven above under g) ror R2: (0 Nal-r=(OAlk)2 Me (O)S=P(OAlk)2 `j II XXI XXII
, f :! Flnally, the action o~ nltrophenyl halides XXIII on starting saltæ II results in 1-~ itropheny~ -3-isopropyl-2,1,3-benzothiadlazin~(4)-one-2,2-dioxldes XXIV; ln the ~ollowing ... .
SChemff f Me denotes an equlvalent o~ an alkali metal, alkaline ~f earth metal or ammonium ion, Hal denotes halogen and ~, ~ t ~ has the meanlngs gi~en abo~e under i) ror R2:

'~l O O
~--IN~ + Hal~ (N2)n )--IN~3 ,``f 02S`N 02$`N
¦ Me ~ (N2)n . j II XXIII XXIV

.
: -' '.

'7V~
O . ZO 30J 824 The starting materials II and III may be reacted with the acld chlorides in stoichlometric amounts or an excess thereof, prererably a ratio of loOl to 1.2 moles of a¢id chloride to 1 mole of starting materlal II or III. The preparation of starting materials II and III ls described in U.S. 3,041,~36 and aerman 1,542,836.
Examples Or tertlary bases ror the reaction or startlng materlals III are trlmethylamine, trlethylamlne, pyridine, ~,3,7-plcollne, lutidine, N,N-dlmethylanillne, N,N-dlmethyl-cyclohexylamine, qulnoline, lsoquinoline, qulnazoline, trl-n-butylamlne, trl-n-propylamine and N-propyldilsopropylamlne.
The rollowing may be used as polar solvents: chloro-benzene, o-, m- and p-di¢hlorobenzene, nitrobenzene, anlsole, toluene, methylene chlorlde, chloroform, 1,1- and 1,2-dl-~: chlQroethane, 1,1,2-trlchloroethane, 1,1,2,2- and 1,1,1,2-tetrachloroethane, substltuted carboxylic amldes such as :~ N-methyl- and N,N-dimethylrormamlde, ketones su¢h as acetone, methyl ethyl ketone, acetophenone and cy¢lohexanone, esters 8uch as methyl acetate and lsobutyl acetate, ethers such as diethyl ether, di-n-propyl ether, dioxane and tetrahydrofuran, and nitrlle~ such as a¢etonitrile, isobutyronitrlle and benzonitrile.
The reactlons are usually carried out in a temperature range o~ from 10 to ~70, pre~erably ~ to +40, C, in the case Or less reactive acid chl~rldes, lt may be neoessary to heat to 110Co EXAMPLE 1 :~
l-formyl-3-iso~ropyl-2,1,3-benzothiadlazin-(4)-one-2,2-. dioxide ~ ~ _ g _ '~

~t~
0.~, 30,824 At room temperature, 32 parts (by weight) o~ a 30% ~by weight) solutlon of a mixture Or ~ormic and acetic anhydrldes (prepared rrom equimolar amounts Or rormlc acld and acetlc acid) ln a mixture of rOrmic and acetlc acid is introduced into a solution of 24 parts of ~-isopropyl-2,1,3~benzothia-diazin-(4)-one-2,2-dioxlde in 120 parts of acetonltrile. The reactlon mixture is stirred for ~ hours at 50C and then concentrated ln vacuo. The residue is taken up in methylene chloride, extracted 4 times wlth 005N caustio solutlon and with water, and dried over magneslum ~ul~ate~ A~ter concentration in vacuo there is obtained 24 parts (90% o~
theory) o~ the desired compound as colorless crystals; m,p.:
90 to 99C (decomposes), benzothladiazln-t4)-one-2,2-dloxlde Over a perlod Or 15 minutes, at 15 to 20C and whlle stlrring, 29.5 parts o~ 2,4-dlchlorophenoxy-y-butyryl ohlorlde is run into a solution o~ 26.2 parts o~ the l-sodium salt o~

3-iæopropyl-2,1,3-benzothiadlazin-(4)-one-2,2-dioxlde in 120 parts o~ aoeton$trlle. The reaction mixture is stlrred ~or 1 hour at 20C and then ~reed rrom solvent in vacuo. The resldue is taken up ln methylene ohloride, extracted 4 tlmes wlth 5% sodium carbonate æolutlon, washed with water and dried over magne~ium sulrateO After concentrat~on in vacuo there is obtained 38 parts (81% o~ theory) Or the desired ¢ompound as a colorless viscous oilO A~ter trlturation with cyclohexane, colorless crystals melting at 106 to 109C are obtained.
The ~ollowing oompounds were obtained analogously-: -- 10 -lO~ Z
o O z. ~0, 824 mupO (c) l-proplonyl-~-isopropyl-2,1,3-benzothladiazln-

(4)-one-2,2-dioxide 103 to 105 l-butyryl- "
l-sec-valeryl- " 69 to 73 l-valeryl- " 39 to 44 1 -isoYaleryl-l-capronyl- " 67 to 69 l-(~-methylvaleryl) " 42 to 50 l-enanthyl- "
l-pelargonyl- " ~ 5 = 1~5128 l-caprinyl- "
l-undeoanoyl- "
l-dode¢anoyl-l-tridecanoyl-l-tetradecanoyl- "
l-pentade¢anoyl- "
l-palmitoyl- " 65 to 67 l-acetoxyacetyl- " 69 to 7 .
l-chloroacetyl- " 106 to 109 . l-dlchloroa¢etyl- "
1 ~-chloropropionyl- " 8~ to 85 ::
dichloro~ropionyl-3-isoprop~1-2,1,3-benzo-thladiazin-(4)-one-2,2-dioxide l-a-chlorobutyryl--¢hlorovaleryl--chlorocapronyl-chloroproplonyl-bromobutyryl- "

, . ~.

7'~ ~
.Z0 30,824 m D (C) l-acryloyl-3-isopropyl-2,1,~-benzo~hladiazin-(4)-one-2,2-dioxlde 71 to 76 l-but-2'-enoyl- "
1-pent~ enoyl~ , 1.5~34 ~-methoxyacetyl- "
l-B-methoxypropionyl-1-7-methoxybutyryl- "
1-benzoyl- " 127 to 131 1-~,naphthoyl- " 120 to 125 1-o-bromobenzoyl-1-p-bromobenzoyl- "
1-m-bromobenzoyl- "
l-p-nitrobenzoyl- "
l-m-nitrobenzoyl- "
1-o-nitrobenzoyl- "
l-phenoxyacetyl- i' 111 to 116 l-p-chlorophenoxyacetyl- " 106 to 111 1-2',4'-dlchlorophenoxy- ~
acetyl " 138 to 143 1-2',4~,5~-trichloro-phenoxyaoetyl- " 164 to 170 1-2~-m~thyl-4'-chloro-phenoxyacetyl- " 161 to 163 i 1-2',4'-dlchlorophenoxy-~-proplonyl- " 105 to 108 1-cyclopentanoyl- "
l-¢yclohexanoyl- n 94 to 96 .

' `7t)~
oxalyl-bis~1-¦3-isopropyl-2,l,3-benzothiadia-zin-(4)-one-2,2-dioxide~ 223 to 224 (decomposes) malonyl-bis- "
succinyl-bis- "
glutaryl-bis- "
adipoyl-bis- "
decane-(1,10)-dioyl-bis-1'- ~'-isopropyl-2',1',3'-benzothiadiazin-(4')-one-2',2'-dioxid~ 128 to 135 1 ~-bromobutyryl-3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide Over a period of 10 minutes, at 10C and while stirring, 22.9 parts of ~-bromobutyryl bromide is introduced into a solution of 24 parts of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and 10.1 parts of triethylamine in 130 parts -of acetonitrile. The reaction mixture is stirred for 10 minutes at 20C and then suction filtered. The filtrate is concen-trated in vacuo, taken up in benzene and washed twice with 5%
sodium hydrogen carbonate solution and twice with water.
Drying and concentration give the desired product in the form of a colorless oil ~nD - 1.5552) which crystallizes upon trituration with petroleum ether; m.p.: 73 to 78C.

3-isopropyl-l-n-butoxY carbonyl-2,1,3-benzothiadiazin -(4)-one-2,2-dioxide.
Over a period of 15 minutes and while stirring, a solution of 15 parts of n-butyl chloroformate in 15 parts of aceto-nitrile is run at 15 to 20C into a solution of 26.2 parts of the l-sodium salt of 3-isopropyl-2,1,3-benzothiadia-zin-(4)-one-2,2-dioxide in 120 parts of acetonitrile. The mixture is stirred for 1 hour at 20C and for 2 hours at 65C.

.......

7(~Z

After concentration has been effected in vacuo the residue is taken up in methylene chloride, extracted 3 times with 0.3N caustic solution and with water, and dried over magnesium sulfate. Concentration gives the desired compound in the form of a viscous oil, which crystallizes upon trituration with petroleum ether; m.p.:48 to 54C.
The following compounds were obtained analogously:
m p. (C) 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide, l-methoXycarbonyl 103 to 105 " l-ethoxycarbonyl 109 to 120 " l-n-propyloxycarbonyl " 1-isopropyloxycarbonyl isobutyloxycarbonyl " l-sec-butyloxycarbonyl " l-tert-butyloxycarbonyl ~ " l-n-pentyloxycarbonyl .~ " 1-(3'-pentoxyloxycarbonyl) " l-cyclopentyloxycarbonyl n-hexyloxycarbonyl " l-n-cyclohexyloxycarbonyl " 1-n-heptyloxycarbonyl " l-n-octyloxycarbonyl " l-n-nonyloxycarbonyl " l-n-decyloxycarbonyl ~ .

' :~ - 14 -.'' .

.:. .
B
~, .

10~'~7V~

m p. (c 3-isopro~yl-2,1,3-benzothiadiazin-(~)-one-2,2-dioxide, l-undecyloxycarbonyl " l-dodecyloxycarbonyl " l-tridecyloxycarbonyl " l-tetradecyloxycarbonyl " l-pentadecyloxycarbonyl " l-hexadecyloxycarbonyl 66 to 68 " l-phenyloxycarbonyl 111 to 115 " l-o-methoxyphenyloxycarbonyl 130 to 133 :
" l-methylmercaptocarbonyl117 to 121 " l-ethylmercaptocarbonyl " l-n-propylmercaptocarbonylnD ~ 1.5553 " l-isopropylmercaptocarbonyl " l-n-butylmercaptocarbonyl " l-p-chlorobenzylmercaptocarbonyl 98 to 100 " l-phenylmercaptocarbonyl " 1-p-methoxyphenylmercaptocarbonyl EXAMPLE .~
l-dimethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazin(4)-one-2,2-dioxide 13.9 parts of the potassium salt of 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide in 15 parts of dimethyl-carbamyl chloride was heated for 5 hours at from 100 to 110C.
There was added 150 parts of a mixture of benzene and ether (1 : 2) and the potassium chloride is filtered off (3.6 parts).
~:~ After 100 parts of a 1 : 2 mixture of ether and petroleum : ether had been added to the filtrate, the crystalline ~roduct was suction filtered and recrystallized from cyclo-:
: ~ - 15 -.

7 ~ ~
~Z. 30,824 hexane. The deslred product, which has a melting polnt o~
from 8~ to 8505C, was obtainedO
The ~ollowing compoundæ were obtalned analogously:
m.~. (C) l-diethylcarbamoyl-3-isopropyl-2~1,3-benzo-thiadiazin-(4)-one-2,2-dioxide 100 to 104 l-dl-n-propylcarbamoyl- n dllsopropylcarbamoyl- " 150 to 152 l-n-dlbutylcarbamoyl- "
l-d$-sec-butylcarbamoyl- "
l-N-methyl-N-n-propoxymethyl-carbamoyl- " ~ 5 = 1.52~9 1-~ '-piperidlnoy~ - " 81 to 84 1-~ exahydro-l'-H-azepln ~ oy~ - " 100 to 103 . l-dlmethylthiocarbamoyl- " 78 to 81 l-diethylthiocarbamoyl- "
l-di-n-propylthlocarbamoyl- "
l-dlisopropylthlocarbamoyl- i' l- ~ '-pheny~-N",Nn-dimethylf'ormamidiny,~7-3-lso-pro~yl-2,1,~-benzothladlazln-(4)-one-2,2-dioxide 1~7 . EXAMrLE 6 l-methylsulrony~ so~roDyl-2Jl~3-benzothiadlazin-(4)-one 2,2-dloxide Whlle stirrlng and at a temperature Or 20C, 12.6 partæ
. ~
of methanesulronyl chlorlde was run over a perlod Or 10 mlnutes lnto a solution o~ 26.2 parts o~ the l-sodlum salt Or ~-isopro~yl-251,3-benzothiadlazin-(4)-one-2,2-dloxlde in 120 p~rts o~ aaetonitrlle. ~he reactlon mixture was stlrred ~or .

7V~
. z o ~o, 824 ~0 mlnutes at 20C and ~or 2 hours at 60 to 65C. The precipltated sodlum chlorlde was ~lltered o~ and the rlltrate concentrated ln vacuo. The residue was triturated in ether, suctlon ~lltered and waæhed with water until neutral; the deslred compound was obtalned ln the ~orm of colorlesæ
crystals melting at 156 to 158C, The ~ollowlng oompounds were obtained ln a slmllar manner:
m.p. (C) l-ethylsulronyl-3-isopropyl-2,1,3-benzothiadlazln-(4)-one-2,2-d~oxide 110 to 112 l-n-propylsulronyl-l-lsopropylsul~onyl-l-butylsulronyl-l-sec-butylsul~onyl- "
lsobutylsul~onyl- " 103 to 110 l-pentyls*lfonyl- "
l-benzenesulronyl- " 162 to 166 l-p-toluenesulfonyl- " 141 to 14 l-p-brcm.d~onesul~onyl- " 16~ to 168 l-o-brom~enzenesulronyl-l-m~brom~be~enesulronyl- "
l-p-nitrobenzen~sul~onyl- " 160 to 175 l-o-nitrobenzenesulronyl-l-m-nitrobenzenesul~onyl- "
l-B-na~hthalenesulronyl- " 106 EXAMrLE 7 l-dimethylsulfamoyl 7-isoproDyl-2~ benzothiadiaz~n-(4) one-2~2-dioxide While stirrlng and at a temperature Or 20C, 15.8 parts ' ~: :

0,Z. 30,824 of dimethylsulramoyl chlorlde in 15 parts of acetonitrile was run over a period Or 10 minutes lnto a solution of 26.2 parts of the l-sodlum salt Or 3~isopropyl-2,1J~-benzothiadlazin-(4)-one-2J2-dioxide ln 120 parts Or acetonitrile. The reaction mixture was stlrred for 4 hours at 65C. The preclpitated sodium chlorlde was filtered off and the filtrate concentrated in vacuo and digested ln 50 parts o~ hot methanol. Insolubles were ~lltered o~f hot and the cold flltrate was triturated.
Suctlon flltration gave colorless crystals of l-dimethyl-sulfamoyl-~-isopropyl-2,1,~benzothiadiazin-(4)-one-2,2-dioxide meltlng at 1~5 to 141C.
The followlng compounds were obtalned analogously:
; m.~. (C) l-diethylsulfamoyl-3-isopropyl-2,1,3-benzothia-dlazin-(4)-one-2,2-dioxide l-di-n-propylsulramoyl-l-methylamlnosul~onyl- " 151 to 15 l-ethylaminosulfonyl- "
l-n-propylaminosulfonyl- "
l-isopropylamlnosulfonyl- " 151 to 153 l-n-butyiaminosul~onyl- "

(4)-one-2,2-dloxide . .
Whlle stirring and at 15 to 20C, a solution oP 2602 parts of the l-sodium salt of ~-iæopropyl-2,1,~-benzothia-diazln-(4)-one-2,2-dioxide ln 120 parts of acetonitrile was i run o~er a perlod o~ 10 minutes into 15.4 parts o~ N-methyl-benzimide chlorlde in 120 parts of acetonitrileO The reaction mixture ., :

.

O~Z0 30,824was stirred ror 1 hour at 20C and then concentrated ln ~acuo.
The residue was taken up in methylene chloride, extracted rOur times wlth 10% sodium carbonate solution~ washed wlth water and driedO Arter concentration ln vacuo the deslred product was lsolated as a viscous oil which crystallized upon trlturatlon wlth petroleum ether; m~p.: 85 to 95Co A sample recrystalllzed rrom cyclohexane melted at 96 to 103C.
~ ethylbenzlmidy~ -3-lsopropyl-2,1,3-benzothladiazln-(4)-one-2,2-dioxlde and 1-~ -n-propylbenzlmidy~ -3-isopropyl-2,1,3-benzothladiazln-(4)-one-2,2-dioxide were prepared analo~ously, 3-lso~ropyl-?,1,3-benzothiadiazln-~4)-one-2,?-dioxlde-1-~,0-dlethylphosphorothloat~
.
At room temperature, 18O9 parts of 0,O~diethylphosphoryl chlorlde was added to a solutlon Or 26.2 parts of the l-sodium ~; salt or 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide ln 120 parts o~ acetonltrile. The mlxture was stirred under rerlux ror 12 hours, and then concentrated in vacuo, taken up in benzene and extracted twlce wlth water, twlce with 10~
sodlum hydrogen oarbonate solution and again twlce wlth water.
A~ter dryln~ and con~entration, the desired compound was ; obtained as a viscous oil; nD5 = 1.5219.
The following compounds were obtalned analogously:
~-lsopropyl-2,1,3-benzothladlazln-(4)-one-2,2 dloxide, 1-~ ,0-dlmethylphos~horothioat~ , n25 = 1.54?4 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide, dl-n-propylphosphorothioat~

: :
. .
.-~ ' .

O.Z0 ~0,824 3-lsopropyl-2,1,3-benzothladiazln-(4)~one-2,2-dloxlde, 1-~ ,0-dlmethylphosphat~
; 3-lsopropyl-2,1,3-benzothladiazin-(4)-one-2,2-dloxide, 1-~ ,0-dlethylphosphat~

l-~erchloromethylthio-~-isopro~yl-2,1 t 3-benzothiadlazin-(4~-one-2,2-dioxide At room temperature and whlle stirring, 19~5 ~arts of per¢hloromethylsulfenyl chlorlde was run over a perlod of 10 mlnutes into a solution o~ 2602 parts of 3-isopropyl-2,1,~-benzothladlazln-(4)-one-2,2-dioxlde ln 52 parts of acetone.
After the reacti~n mlxture had been stlrred ~or 1 hour at 20C
the preclpitated salt was remo~edO A~ter conoentration ln Yacuo the residue was taken up ln methylene chlorldeJ washed three times with 0~3N caustic solutlon and wlth water, and dried o~er magneslum sulfateO A~ter oonoentration in ~acuo, the desired product was obtained ln the rOrm Or a vlscous oil;
~ upon trituration with petroleum ether the substance j ¢rystalllzed; m.p.: 77 to 80C.
EXAM~IE 11 .~, . .. .
~
At 20C, 27.8 parts o~ the ~otasslum salt o~ ~-isopropyl-2,1,3-benzQthiadiazin-(4)-one-2,2-dioxide was suspended ln 150 parts by volume Or a¢etonitrile; a solution of 27.1 parts of picryl chloride in 50 parts by ~olume of acetonttrile was ~, then drlpped ln. The mixture was re~luxed ror 3 hours;
subsequently, the potassium chlorlde was filtered of~ (6.2 parts) a~d the flltrate concentrated. The residue ¢rystallized o~
OOZ. 30,824 upon trituratlon wlth a mixture of ether and petroleum ether.
The desired compound w~s obtained in the rorm of yellowish red crystals; mOp.~ 110 to 115C (153 to 157C a~ter recrystalllzation ~rom carbon tetrachloride)~
Appllcation may be e~ected ~or instance in the ~orm o~
directly sprayable solutions, powders, suæpenslons (lncludlng hi~h-percentage aqueous, olly or other suspenslons), d~spersions, emulsionæ, oil dispersions, pastes9 dusts, broadcaætlng agents, or granules by ~praying, atomlzlng, ; 10dusting, broadeasting or waterlng. The ~orms of appllcation depend entlrely on the purpose ~or whlch the agents are belng used; ln any caæe they should ensure a ~ine distributlon o~
the active ingredient For the preparatlon o~ ~olutions, emulslons, pastes and oil dlspersions to be sprayed dire¢t, mineral oll ~raotions oP medlum to hl~h boillng point, such as kerosene or dlesel oll, further coal-tar oils, etc, and olls of ~egetable or animal orlgin, aliphatic, oycll¢ or aromatic hydrocarbons such as benzene, toluene, xylene, paraffln, tetrahydronaphthalene, alkylated naphthalenes and their derivatlves such as methanol, ethanol, propanol, butanol, chloro~orm, carbon tetra¢hlorlde, oyclohexanol, ¢yclohexanone, chlorobenzene, isophor~ne, et¢., and strongly polar solvents such as dlmethyl~ormamide, di-methyl sul~oxide, N-methylpyrrolidone, water, etc. are suitable.
~Aqueous ~ormulations may be prepared ~rom emulsion J~concentrate3, pastes, oll dispersions or wettable powders by adding waterO T~ prepare emulslons, pasteæ and oll dispersions the ingredients as such or dissolved in an oil or solvent may - 21 _ .

7V~
. z ~ 30, 824 be homogenlzed in water by means of wettlng or dlspersing agents, adherents or emulsifiersc Concentrates which are sultable for dllution wlth water may be prepared from actlve lngredlent, wettlng agent, adherent9 emulsl~ying or disperslng agent and posslbly solvent or oilO
Examples Or surractants are: alkall metal, alkaline earth metal and ammonlum salts of ligninsulfonic acid, naphthalene-sulronic acids, phenolsulfonic acids9 alkylaryl sulronates~
alkyl sul~ates, and alkyl sul~onates, alkali metal and alkaline earth metal salts o~ dlbutylnaphthalenesul~onic a¢id, lauryl ether sul~ate, fatty alcohol s~l~ates, alkall metal and alkaline earth metal salts o~ fatty aclds, salts of sul~ated . . , hexadecanols, heptadecanols and octadecanols, salts of sulrated fatty alcohol glycol ether, ¢ondensatlon products Or sulronated naphthalene and naphthalene derivatives with ~ormaldehyde, condensatlon produ¢ts of naphthalene or . naphthalenesulfonio acids with phenol and rormaldehyde, poly-tl' oxyethylene octylphenol ether, ethoxylated isooctylphenol, ethoxylated oct~lphenol and ethoxylated nonylphenol, alkyl-phenol polyglycol e~hers, tributylphenol polyglycol ethers, alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, ., lignin, sul~lte waste llquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared I by mlxlng or grlndlng the actlve ingredients wlth a solld - ¢arrier.
Granules, e.~., coated, lmpre~nated or homogeneous '7~ ~
OOZ~ 30,824 granules, may be prepared by bondlng the active lngredients to solld carrlers. Examples of solld carrlers are mlneral earths such as slliclc acid, sillca gels, sillcates, talc, kaolin, Attaclay, l~mestone, llme, chalk, bole, loess, clay, dolomlte, diatomaceous earth, calclum sul~ate, magnesium sul~ate, magnesium oxide, ground plastlcs, ~ertllizers such as ammonium sul~ate, ammonlum phos~hate, ammonlum nitrate, and ureas, and vegetable products such as graln flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
The rormulations contaln from 0.1 to 95, and preferably 0,5 to 90, % by weight o~ a¢t ~e lngredient.
There ~ay be added to the compositions or indlvidual active ingredients (lf deslred, lmmediately berore use (tank-mlx)) oils o~ varlous types, wetting agents or adherents, herbicides, fungi¢ldes, nematocldes, lnsectlcides, bacterlcides, trace elements, ~ertilizers, anti~oams (e.g., slllcones), growth regulators, antldotes and other herblcldally errectlve compounds suoh as substltuted alkylsulfonylglycolic amldes and lmideæ
substltuted alkylamlnosulronylglycolic amides and imldes substltuted acetanllldoalkyl sul~ltes substituted anilines substltuted azides -substltuted aryloxycarboxylic acids and aryloxythlocarboxyll¢
aolds and salts, esters and amides thereo~, substituted alkanols, alkenols substituted ethers substltuted arsonic aclds and arsen~c aclds and salts, esters and amldes thereo~
- 2~ -;
.
.
.

OOZ. 30,824 substituted benzene sulronamides substltuted benzimidazoles substituted benzlsothlazoles substltuted dihydrobenzo~uranyl alkylamino sul~onates subætituted benzothiadiazinone dloxides substituted benzoxazines substituted benzoxazinones substituted benzoxazollne thiones substituted benzothiadiazoles substituted benzothiazollnyl alkyl carboxyllc acids and salts, esters and amides thereor .- substltuted blurets substituted qulnolines substituted carbamates substituted allphatic or cycloaliphatic carboxyllc aclds and i thlocarboxyllc acids and thelr salts, esters and amides substltuted aromatlc carboxylic aclds and thiocarboxyllc acids ~, and their salts, esteræ and amides substituted oarbamoylalkylthlol- or -dlthiophosphates substttuted qulnazolines substituted cycloalkylamldocarbothiolic aoids and thelr salts, esters and amldes substltuted cycloalkylcarbonamidothlazoles substituted dlcarboxyllc acids and thelr salts, esters and amldes 1 substltutsd dihydrobenzo~uranyl sulronates ; substituted dlhydropyran dlones substituted disul~ides substituted dioxanes ' .

o.z. ~o,824 substituted dipyrldyllum æalts substltuted dlthlocarbamates substltuted dithi.ophosphoric aoids and their salts, esters and amldes substltuted ~luorenecarboxylic aclds and their saltæ, esters and amldes substltuted ureas substltuted hexahydro-lH-carbothloates substituted hydantolns substituted hydrazides substituted hydrazonlum salts substituted hydroruranones substltuted isoxazole pyrimldones ;i substituted imidazoles substltuted imidazolidinedlone oarboxàmldes substituted lsothiazole pyrimldones substltutçd ketones ~-;
substituted naphthoquinones substltuted naphthallo anhydrldes -:
substltuted allphatic nltrlles substituted aromatlc nitrlles substltuted oxadiazoles substituted oxadiazlnones substituted oxadlazolines substltuted oxadlazolldlne diones .
substltuted oxazolldines . 3ubstituted oxadiàzlne diones substitutad oxazole pyrlmld~nones substltuted phenols and their salts and esters . .

. :~

7~ ~
o.z. ~0,824 substltuted phosphonic aclds and thelr salts, esters and amldes substituted phosphonlum ch'or~des substituted phosphonalkyl glyclnes substituted phosphites substituted phosphorlc acids and their salts, esters and amides substituted piperidines substituted pyrazoles 0 substituted pyrazole alkylcarboxylic acids and thelr salts, esters and amides substituted pyrazollum salts substituted pyrazollum alkyl sulrates substituted ~yrldazlnes substltuted pyridazones substltuted pyrldlne oarboxylic acids and their salts, esters and amides substituted pyridlnes substltuted pyrldlne carboxylates substltuted pyridinones substituted pyrimidines substltuted pyrimidones substituted pyrrolidine carboxylic acid and lts salts, esters and amides ~ -substituted pyrrolidines substltuted pyrrolldones substltuted arylsulronic acids and their salts, esters and amldes substituted sulramates : :.

70 ~
.Z~ 30,824 substltuted styrenes substituted sulronyl toluidldes substltuted tetrahydrooxadiazlne diones substituted tetrahydroxadiazole diones substituted tetrahydromethanoindenes...
æubstltuted tetrahydroxadlazole thlones substituted tetrahydro~hladiazlne thiones substituted tetrahydrothladiazole dlones substltuted aromatlc thlocarbonylamides substituted thlobenzamldes substltuted thlocarboxyllc aclds and their salts, esters and -- amldes ; substituted thlol carbamates .
; substituted thloureas subætituted thlophosphorlc acids and their salts, esters ; and amldes . subætituted triazlnes - substituted trlazlnones substltuted trlazoles .~ 20 substltuted uraclls substituted uretldlne diones chlorates, and substituted azetidine ¢arbothioates.
. The last-mentioned herbi¢idal compounds may also be a~plied be~ore or after the active ingredients or compositlonæ
thereor according to the lnvention~
Theæe agents may be added to the herblcides aocordlng to the invention in a ratlo by welght Or from 1 : 10 to 10 : 1, , ,-1 I The same applies to olls, wettlng agents and adhèrents, ... - 27 -'7~'~
O.Z. 30J824 ~nglcldes, nematocldes, insectlcldes, bacterlcides, antldotes and growth regulators.
The agents o~ the lnvention may be used once or several times before or after planting, before sowlng, and berore, during or after emergence o~ the crop plants and unwanted plants.
The new compositions ha~e a strong herbicidal action and may therefore be used as weedkillers or for controlling the growth Or unwanted plants. Whether the new actlve lngredlents are used as total or selective agents depends in essence on the amount o~ ingredient used per unlt area.
; Ey weeds and unwanted plant growth are meant all mono-cotyledonous and dicotyledonous plants whlch grow ln locl where they are not desired.
The agents according to the invention may therefore be used ~or ¢ontrolllng ~or instance Gramineae, such as Cynodon spp. Dactylls spp.
Dlgitaria spp. Avena spp.
-, 20 Echinochloa spp. Bromus spp.
Setaria spp. Uniola spp.
Panicum æpp~ Poa cpp.
Alopecurus spp. Leptochloa spp.
; Lollum s~p. Brachiarla spp.
Sorghum spp. Eleuæine spp.
Agropyron spp~ Cenehrus spp, Phalaris spp. Eragrostis sp~, Apera sppO rhragmltres communis etc,;

:

lO~ l)Z
o.z. 30,824 Cyperaceae, such as Carex sppO Eleocharls spp.
Cyperus spp, Scirpus spp.
etc.;
dicotyledonous weeds, such as Malvaceae, e.g., - Abutllon theoprasti Hlbiscus spp. ;-Slda sppO Malva sppO `etc.;
Compositae, such as Ambrosia spp. Centaurea spp.
La¢tuca spp. Tussilago spp.
Senecio spp. Lapsana communis Sonchus spp. Tagetes spp.
Xanthium spp. Erigeron spp~
Iva spp. Anthemls spp.
Gallnsoga spp. Matricaria spp.
Taraxacum spp. Artemisia 8pp.
Chrysanthemum spp. Bidens spp.
~, 20 Cirslum spp. etc., Convolvulaceae, such as Convolvulus s~p. Cuscuta spp.
Ipomoea spp. Jaquemontia tamni~olia .
etc.;
Crucirerae, such as ; Earbarea vulgaris Arabidopsis thaliana Br~ssica æpp. Descurainia spp.
Capsella spp. Draba spp.
Slsymbrium spp. Coronopus didymus - 29 _ ..~

-.. . . ~ , . ..
,. . . . . .

70 ~
O.Z. 30,824 Thlaspi spp. Lepidium sppO
Sinapis arvensls Raphanus spp, etc.;
Geraniaceae, such as Erodium spp. Geranium spp.
etc.;
Portulacaceae, such as Portulaca spp. etc.;
Primulaceae, such as Anagallis arvensis Lysimachia spp.
etc.;
; Rubiaceae, such as Richardla spp. Diodia 9pp, Galium spp. etc.;
Scrophulariaceae, su¢h as Llnarla spp. Digitalls spp.
Veronlca spp. etc, -, Solanaceae, such as !
Phyæalls æpp. Nicandra spp.
Solanum spp. Datura spp.
etc.;
Urticaceae, such as ~; Urtica spp.
Violaceae, such as Viola spp. etc.;
Zygophyllaceae, such as Tribulus terrestris etcO;
, Euphorblaceae, such as Mer¢urlalls annua Euphorbia spp.

' .

: .

7~ ~
O.Z. 30,824 Umbelliferae, such as Daucus carota Amml maJus Aethusa cynap~um etc.;
Commelinaeae, such as ~-~
Commellna spp. etc,;
Lablatae, such as Lamlum spp. Galeopsis spp.
etc.:
Legumlnosae, such as Medicago spp. Sesbania exaltata ~rifollum spp. Cassia spp.
Vicla sppO Lathyrus spp.
etc.;
i Plantaginaceae, such as ~- Plantago spp. etc.;
~olygonaceae, such as ~olygonum spp. Fagopyrum spp.
, Rumex spp. etc.;
Aizoa¢eae, such as Mollugo verticillata etc.
Amaranthaceae, such as Am~ranthus spp. etc.;
Boraglnaceae, suoh as j Amsinckla spp. Anchusa spp.
Myostis spp. Llthospermum spp.
etc.;
' Caryophyllaceae, such as Stellaria spp. Silene spp.
Spergula spp. Cerastlum spp.

.~ ' .
.~
.
': . :: . ~ , ;, ' 0 ~ ~ 7~ ~
O.Z. 30,824 Saponarla spp. Agrostemma glthago Scleranthus annuus etc.;
Chenopodlaceae, such as Chenopodium spp. Atriplex spp.
Kochla spp. Monolepsis nuttalliana Salsola Kali etc.;
Lythraceae, such as Cuphea spp. etc.;
Oxalidaceae, such as Oxalis spp.
Ranunculaceae, such as Ranunculus spp. Adonis 8pp, I Delphinium 9pp, etc.
, rapaveraceae, su¢h as ~apaver spp. Fumaria officinalis ` etc.;
Onagraceae, such as Jussiaea spp. etc.;
l :
i Rosaoeae, such as Alohemlllia spp. Potentilla spp.
etc,;
~otamogetonaceae, such as Potamogeton spp. etc.;
Na~adaceae, such as ~3a3: 9~p. etc.
Marsileaceae, such as Marsilea quadri~olla etc.
, The herbicldes according to the in~ention may be employed ;
in cereal crops suoh as '' :.
":
.,.................. ~ .

`` ~0~ 702 o,z, 30,8~4 Avena spp. Sorghum Tritlcum spp. Zea mays Hordeum spp~ ~anlcum mlllaceum Secale ~pp. Oryza spp~
and ln dlcotyledon crops such as Crucirerae, e.g5 Brassica spp. Raphanus spp.
Sinapis spp. Lepidlum spp.
Compositae, e.g.
Lactuoa spp. Carthamus spp.
Hellanthus spp. Scorzonera spp.
Malvaceae, e,g.
Gossyplum hirsutum , Leguminosae, e.g.
Medicago spp. Phaseolus spp.
Tri~clium spp. Arachis spp.
~isum spp. Glycine max.

Chenopodlaceae, e.g.
Beta spp. Spinacla spp.
Solanaceae, e.g.
;~ Solanum spp. Capsicum annuum ' Nicotianla spp.
. . . ~
Llnaceae, e.g.
Llnum spp.
Umbelli~erae, e.gO
Petrcsel~num spp. Apium graveolens Daucus carota Rosaceae, e.g. Fragaria Cucurbitaceae, e,g.
- 3~ -', ~
.

- , .
.

10~ 7V~
o . zO ~o, 824 cuaumis 5pp. Cucurbita spp.
Lillaceae, e.g.
Allium spp~
Vitaceae, e.g, Vitls vlnifera Bromellaceae, e.gO
Ananas sativus.
The amount used of the agents according to the invention may vary and depends in essence on the type of e~ect to be achleved, lt is generally ~rom 0.1 to 15 (and more), pre~erably from 0.2 to 6, kg per hectare of actlve lngredisnt.
EXAM~LE 12 In the greenhouse, cotton (Gossypium hlrsutum) ln~ested to a considerable extent with wild mustard (Slnapis arvensls) wa~ treated at a growth helght Or ~rom 2 to 10 cm wlth 1 kg/ha of each o~ the followlng active lngredlents, each belng emulslfled or dlspersed in 500 llters Or water per hectare:
I 3-i~o~ropyl-2,1J~-benzothiadlazin-(4)-one-2,2-dioxide, l-ethylcarbamate lsobutylsulfonyl-3-isopropyl-2,1,3-benzothladiazin-(4)-one-2,2-dioxide III l-ethylsul~onyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxlde IV l-diethylcarbamoyl-3-lsopropyl-2,1J:3-benzothiadiazin-(4)-one-2,2-dioxide, After 2 to 3 wee~s it was ascertained that compounds I to IV had better crop plant compatiblllty than XIV ~-isopropyl-2,1,7-benzothiadiazin-~4)-one-2,2-dioxlde.
The results are given below:

, ~

.' .

. . . . - , . . .
.

10~702 oOz. ~o,824 Actlve lngredlent I II III IV XIV
kg/ha 1.0 1.0 1.0 1.0 _ 1.0 .~ ~ . .
Gossyplum hlrsutum 0 0 0 10 30 Unwanted ~lant:
Slnapis arvensls 100 100 100 100 100 0 = no damage 100 = complete destruction In the greenhouse, varlous plants were treated at a growth height Or ~rom 2 to 25 cm with 4 k ~ ha o~ each of the ~ollowing compounds, each being dispersed or emulsi~led in 500 llters of water per hectare:
I 3-isopropyl-2,1,3-benzothiadlazln-(4)-one-2,2-dloxide, l-ethylcarbamate II l-isobutylsul~onyl-3-isopropyl-2,1,3-benzothladiazin-:l 10 (~)-one-2,2-dioxlde .: I
III l-ethylsulronyl-3-lsopropyl-2,1,3-benzothladiazin-(4)-one-2,2-dioxide IV l-diethylcarbamoyl-3-lsopropyl-2,1,~-benzothiadiazin-(4)-, one-2,2-dloxlde l-dimethylcarbamoyl-3-isopropyl-2,1,3-benzothiadlazln-(4)-one-2,2-dloxlde .
' VI 1-N-methyl-N-n-propoxymethylcarbamoyl-3-lsopropyl-2,1,3--l benzothiadlazin-(4)-one-2,2-dioxide . VII l-dimethylthiocarbamoyl-3-isopropyl-2,1,3-benzothiadlazln-(4)-one-2,2-dioxide VIII l-B-naphthalenesul~onyl-3-isopropyl-2~ -benzothiadla-zln-(4)-one-2,2-dloxide OOZ. 30,824 IX l-isopropylaminosulfonyl-3-lsopropyl-2,1,3-benzothia-diazin-(4)-one-2,2-dloxide X l-methylamlnosulfonyl-3-lsopropyl-2,1,3-benzothiadiazln-(4)-one-2,2-dioxide XI 1-(2',4',6'-trlnitrophenyl)-~-isopropyl-2,1,3-benzo-thladiazln-(4)-one-2,2-dioxlde XII 3-isopropyl-2,1,3-benzothladlazin-(4)-one-2,2-dioxlde, l-methylcarbamate ; XIII 3-iso~ropyl-2,1,~-benzothiadiazin-(4)-one-2,2-dioxide, l-phenylcarbamate, After 2 to 3 weeks it was ascertained that the actlve ingredients had very good crop plant compatiblllty and a good herbicldal action.
The results are glven below:

, . . ., . - :.
Crop ~lant#:
I Oryza sati~a O O O O O O O
Glycine max. O O O O O O O
Sor~hum blcolor O O O O O O O
Zea mays O O O O O O O
Trlticum aestivum O O O O O O O
Hordeum vulgare O O O O O O O
Secale cereale O O O O 10 0 Solanum tuberosum O O O O O O O

. Sinapis arvensls 100 lOO lOO 100 100 100 100 Cyperus esculentus 80 75 75 90 100 85 90 , , .' _ ~6 -: '' '7V ~

o z. ~o,824 Actlve ingredient VIII IX X XI XII XIII
Cro Dlants.
Oryza sativa O O O O O O
Glycine max. O O O O O O
Sorghum blcolor O O O O O O
Zea mays O O O O O O
Tritlcum aestlvum O O O O O O
Hordeum vulgare O O O O O O
Secale cereale O O O O O O
Solanum tuberosum O O O O O O
Unwanted Plants:
; Sinapis ar~ensls 100 100 100 100 100 10~
Cyperus esculentus 95 80 90 75 100 70 O = no damage 100 . complete destruction RXAM~LE 14 In the greenhouse, loamy sandy soil was filled lnto pots and sown with the seeds o~ ri¢e (Oryza sativa), wheat (Triticum aestivum) and wild mustard (Sinapls arvensis). The soil was then immediately treated with 3 kg/ha o~ l-dléthyl-carbamoyl-3-isopropyl-2,1,3-benzothi~diazin-(4)-one-2,2-dioxlde (IV) and ~ kg/ha of ~-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide, l-methylcarbamate (XII), eaoh compound being emulsified or disper~ed in 500 liters of water per heotare.
After 4 to 5 weeks it was ascertained that the a¢tive ingredients had excellent crop plant ¢ompatibllity and a good herbicidal action.
The results are given below:

7 0 ~
~Z. 30,824 Active ingredlent IV XII
Cro~ plants:
Oryza satlva O O
;~ Tritlcum aestivum O O
Ya~ e~D~}
Slnapis arvensls 90 90 O = no damage, 100 = complete destruction.
The action of the followlng compounds corresponds to that o~ the actl~e ingredients employed in Examples 12, 13 and 14:
l-(N'-phenyl-N",N"-dlmethylformamidlnyl)-~-lsopropyl-2,1,~-benzothiadlazin-(4)-one-2,2-dioxide (XV) -~-isopropyl-2,1,~-benzothiadiazin-(4)-one-2,2-dloxide-; l-p-chlorobenzylmercaptocarbamate (XVI) ~-lsopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide-~- 10 l-methylmercaptocarbamate (XVII).
ExAMrLE 15 90 parts by weight of the compound o~ Ex~mple 1 is mixed wlth 10 parts by weight o~ N-methyl-a-pyrrolldone. A mixture is obtained whlch is suitable ~or application in the form of very fine drops.

- 20 parts by wei~ht of the compound of Example 2 is dlssolved in a mixture consistlng of 80 parts by welght o~
xyleneJ 10 parts by welght of the adduct of 8 to 10 moles of ethylene oxide to 1 mole Or oleic acld-N-monoethanolamlde,

5 parts by welght of the calcium salt of dodecylbenzenesulfonlc - 20 acld, and 5 parts by wei~ht of the adduct of 40 moles of ethylene oxide to 1 mole of castor oll. The composltion , . ... ! . ~

7V~
O.Z. 30,824 contalns approx. 16.7% of actlve ingredient. By pouring the solution lnto water and unl~ormly distrlbuting lt thereln, a spray llquor is obtained.
EXAMrLE 17 20 parts by welght Or the compound of Example 3 ls dissolved in a mixture con~lsting of 40 parts by welght o~
cyclohexanone, ~0 parts by weight Or lsobutanol, 20 parts by weight of the adduct Or 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by welght Or the adduct Or 40 moles Or ethylene oxlde to 1 mole Or castor oil.
EXAM~1E 18 20 parts by welght o~ the compound of Example 4 1~
dlssolved in a mlxture conæiætlng o~ 25 parts by weight of ! cyclohexanol, 65 parts by weight o~ a mineral oll ~ractlon haYing a bolling polnt between 210 and 280C, and 10 parts by welght or the adduct of 40 moles of ethylene oxide to 1 mole Or castor oll.
EXAMrLE 19 20 parts by welght of the compound or Example 5 is well mlxed wlth 3 parts by weight Or the sodium salt of dlisobutyl-naphthalene~-sulronlc acid, 17 parts by weight or the sodium salt or a ligninsulfonic acld obtalned ~rom a sul~ite waste liquor, and 60 parts by weight of powdered sllica gel, and triturated in a hammer mill.
ExAMr~E 20 3 parts by welght or the compound of Example 6 is intimately mixed with 97 parts by welght of particulate kaolin, A dust is obtalned contalnlng 3~ bg welght of the active ingredient.
- 39 ~

:

,-' "

lV&1;~'702 o.z. 30,824 30 parts by weight of the compound o~ Example 7 is intimately mixed with a mixture consisting of 92 parts by weight o~ powdered sllica gel and 8 parts by weight of para~fin oil which has been sprayed onto the surface Or this silica gelO A formulatlon of the acti~e lngredient is obtained havlng good adherence, In the greenhouse, various plants were treated at a growth height of from 2 to 18 cm with 2 kg/ha of each or the following active ingredients, each being dlspersed or emulslfled in 500 liters of water per hectare:
I l-phenoxyacetyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide II l-p-chlorophenoxyacetyl-3-isopropyl-2,1,3-benzo~hiadlazin-(4)-one-2,2-dioxide III 1-2',4'-dlchlorophenoxyacetyl-3-isopropyl-2,1,3-benzo-thiadiazin-(4)-one-2,2-dioxide 1-2',4'-dichlorophenoxy-~-proplonyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide VII l-chloroacetyl-3-isopropyl-2,1,~-benzothiadlazin-(4)-one-2,2-dioxide VIII l-acetoxyacetyl-3-isopropyl-2,1,3-benzothladiazin-(4)-one-2,2-dioxlde IX l-propionyl-3-isopropyl-2,1,3-benzothiadiazin(4)-one-2,2-dioxide X l-~-chloropropionyl-3-isopropyl-2,193-benzothiadiazin- :~
(4)-one-2,2-dioxide XI l-~-bromobutyryl-3-lsopropyl-2,1,~-benzothiadiazln-(4)-"

10~;~7V~
.Z. 30,824 one-2,2-dioxide XII l-sec-valeryl-3-isopropyl-2,1J3-benzothiadi æln-(4)-one-2,2-dioxide XIII ~-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxlde-l-(O,O-dimethylphosphorothloate) xrv 3-isopropyl-2,1,3-benzothladlazln-(4)-one-2,2-dioxide-l-(O,O-diethylphosphorothloate) XV oxalyl-bls-l-~ -isopropyl-2~1,3-benzothladiazln-(4)-one-. 2,2-dioxid~
XVI l-palmitoyl-3-isopropyl-2,1,3-benzothladiazln-(4)-one-2,2-dioxide ~ XVII 1-~ormyl-3-isopropyl-2,1,~-benzothiadlazin-(4)-one-2,2-:~ dloxide After 2 to 3 weeks it was ascertained that the actlve : ln~redients had a good herbloidal action and ex¢ellent crop plant compatibility.
The results are given below:
~^ Active ingredient I II III V VII VIII IX X
: ' Crop plants:
Trltlcum aeætivum O O O O O O O O
. Hordeum vulgare O O O O O O O O
~; Secale cereale O O O O O O O O
. ~ .
Qryza sativa O O O O O O O O
.,'", Glycine rnaxO
; ~, .;
~-Sinapis arvensls95 100 90 95 100 100 90 95 ..

'.' ~ ^ .

O ~ Z 7 30,824 Actlve lngredient XI XII XIII XIV XV XVI XVII
k ~ ha 2 2 2 2 2 2 2 Triticum aestivum O O O O O O O
Hordeum vulgare O O O O O O O
Secale cereale O O O O O O O
Oryza sativa O O O O O O O
Gylclne max O O O O O O O
Sinapis arvensis 95100100 95 90 90 90 O = no damage, 100 = complete destruction.

In the greenhouse, loamy sandy soll was filled into pots and sown with various seedsO The soll was then immedlately treated with 3 k ~ ha o~ each of the following active ingredients, each being dispersed or emulsi~ied in 500 liters of water per hectareo p-chlorophenoxyacetyl-3-isopropyl-2,1,3-benzothladiazln-(4)-one-2,2-dioxide III 1-2',4'-dichlorophenoxyacetyl-3-isopropyl-2,193-benzothia-diazin-(4)-one-2,2-dioxide IV 1-2'-methyl-4'-chlorophenoxyacetyl-3-isopropyl-2,1,3-` benzothiadlazin-(4)-one-2,2-dioxide :~
V 1-2',4'-dlchlorophenoxy-~-proplonyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dloxide VIII l-acetoxyacetyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dloxide IX l-propionyl-3-isopropyl-2,1,3-benzothiadiazin-(4)~one-2,2-dioxide X l ~-chloropropionyl-3-isopropyl-2~1,3-benzothiadiazin~(4)-. 20 one-2,2-dioxide . - 42 -.. . ~ :.
.

lO~;Z7~3Z
O,Z. 30,824 XIII 3-lsopropyl-2,1,3-benzothiadiazln-(4)-one-2,2-dioxide-l-(O,O-dimethylphosphorothioate) XIV 3-isopropyl-2,1,3-benzothladlazin-(4)-one-2,2-dioxide-l-(O,O-diethylphosphorothioate) After 4 to 5 weeks it was ascertained that the active ; ingredients had a good herbicidal action and excellent crop plant compatibility.
The results are given below:
Active ingredient II III IV V VIII IX X XIII XIV
~ .
Cro~ plants:
Zea mays O O O O O O O O O
Tritiaum aestivum O O O O O O O O O
Oryza sativa O O O O O O O O O
Glycine max. O O O O O O O O O
Gossypium hirsutum O O O O O O O O O
:
'' U~e~d Slnapis arvensis 100 95 95 100 80 90 80 80 100 O = no damage 100 = complete destruction.

In the greenhouse, various plants were treated at a growth height o~ from 2 to 10 cm wlth 1 k ~ ha (in the case of the crop plant) and 0.8 k ~ ha (ln the case of the unwanted plants) of each o~ the follow~ng actl~e ingredients, each bei~g dispersed or emulsif~ed ln 500 liters of water per hectare:
VII l-chloroacetyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide VIII l-acet~xyacetyl-~-isopropyl-2,1,3-benzothladiazin-(4)-one-- 4~ -'';

. ' '' ~' .

7 ~ ~
O.Z. 30,824 2J2-dioxide X l-~-chloropropionyl-~-isopropyl-2,1,3-benzothiadlazin-(4)-one-2,2-dicxide XIII 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dloxlde-l-(0,0-dlmethylphosphorothioate) ; and, ~or comparlson, XIX 3-isopropyl-2,1,3-benzothiadiazlnone-(4)-2,2-dioxide.
A~ter 2 to 3 weeks lt was ascertained that the actlve ingredients VII, ~III, X and XIII had better crop plant : 10 compatibility than, and the same herbicidal actlon as, compound XIX.
The results are given below:
. Active ingredlent VII~III X XIII XIX
k~;/ha o.8 1 0.8 10.8 1o.8 1 o.8 Crop ~lant:
Gossypium hirsutum - O - 10 - O - O - ~0 . Unwanted plants:
. Sinapis arvensis100 - 95 - 95 - 100 - 95 Matrlcaria chamomilla 100 - 96 - 95 - 100 - 95 -0 = no damage, 100 = complete destruction.
. The action of l-pelargonyl-~-lsopropyl-2,1,3-benzothia-diazin-(43-one-2J2-dioxide and 1-pent-3'-enoyl-3-lsopropyl-2,1,~-benzothiadiazin-(4)-one-2,2-dioxide corresponds to that of the active ingredients employed in Examples 22, 2~ and 24.

In the greenhouse, various plants were treated at a :~
growth height o~ ~rom 5 to 15 cm with 2,0 kg/ha o~ each o~ the ~ollowing active lngredients, each being dispersed or . ,.j .
emulsifled in 500 liters o~ water per hectare:
~ - 44 ~

.:

.... . . . . . .
;~ :

70;~
0,Z, 30,824 A l-sec-~aleryl-~-lsopropyl-2,1,~-benzothiadiazln-(4)-one-2,2-dioxlde B 3-isopropyl-2,1,~-benzothiadlazin-(4)-one-2,2-dioxlde-l-phenylcarbamate C 1-~ -methylbenzimidy~ -3-isopropyl-2,1,3-benzothladlazin-(4)-one-2,2-dioxide During the experlment 20 mm o~ preclpltate was added, wlth the exception of Zea mays, which received 60 mm, and Glycine max,, which recelved 180 mm.
A~ter 3 to 4 weeks it was ascertained that active ingre-dients A, B and C had good compatlblllty wlth Zea mays, caused reasonable damage to alyclne max., and had a strong herbicidal action on Bidens pilosa and Chrysanthemum segetum. Compound A
also had a good herbicldal action on Anthemis nobilis, whereas the actlon of B and C was weaker here.
; The results of this experiment, which are glven below, confirm that broadleaved weed species ¢an be controlled in Gram~neae crops and soybeans:
Active ingredient A B C
k~/ha 2.0 2.0 2.0 Crop plants:
Glycine max. 10 (3)* 15 (2) 20 (1) Zea mays 6.6 (~j lO (2) 0 (1) Unwanted plants:
Anthemis nobllis 95 (1)60 (1) 40 (1) Bidens pllosa 90 (1)95 (1) 95 (1) ~ . . .
- Chrysanthemum segetum 95 (1)95 (1) 95 (1) O = no damage, 100 = oomplete destructlon~
* The ~igures in brackets indicate the number o~ experlments 101~;~702 0. z. ~o, 824 carrled out; in the case of more than one experlment, the result is the average obtained.

In the greenhouse, various plants were treated at a growth ; height o~ from 10 to 17 cm with 1.5 ~g/ha of active ingredlent C emuls~fled in 500 l~ters of water per hectaret During the experiment Oryza sativa received 280 to 300 mm o~ precipltate, and Ammanla coccinea 50 to 60 mm.
After 3 to 4 weeks it was ascertalned that the compound had a strong herbicidal action and good crop plant compatibill-ty.
The results o~ this experlment - given below - indicate that marsh and water weeds can be controlled in rlce fields:
Aotive ingredient C
~, ,. ~ , Crop plant:
Oryza ~ativa 5 (2)~
Unwanted plant:
Ammania coccinea 97,5 (2) , , ~. ~.
0 = no damage, 100 = complete destructlon.
f The ~igures in brackets indicate the number of experiments I carried out; the results are the averages obtained.
EXAMPLE 27 ~ ;
In the open, various plants were treated at a growth height o~ ~rom 2 to 14 cm with the following actlve ingredients~
H ~ CH3 ; B ~ - CH~
'S2 , o=c-o~3 r ~
' - 46 -': ~
. .
,.

': :
,~,,~, . . .

~: ~ . ,-.
, . ~

7 ~ Z
ODZ. 30~824 O

D ~ N~02 CH
S=C-N CH
O

E ~ ~-C CH~

SO -NH-CH
O
1I H ~ CH
F ~ N-C CH3 ~C N~CH20C3H7 ; ~ CH~
The application rate was ~.0 kg/ha or each ac~ive lngredient + 2 llters per hectare Or a spreader sticker (adduct o~ 6 to 7 moles o~ ethylene oxlde to 1 mole of iso-oatylphenol), these amounts belng dlspersed or emulsified in 500 liters of water per hectare. During the experiment 20 to ~0 mm of rain fell.
- After 3 to 4 weeks it was ascertained that the compounds ~'B, D, E and F ha~ a good to very good herbicidal action on the dicotyledonous weeds Chenopodium album, Galinsoga parvi~lora, Gallum aparine, Matricaria chamom~lla, Polygonum persicaria, Sinapls arvensis and Stellaria media. Amaranthus retrorlexus was also controlled well by compounds B, D and E, whereas substance F had a poorer action here. The crop plant, rice, was only damaged to a slight extent by B, D, E and F.
~The results are given below:

; - 47 _ .
, ':

7~3Z
o . z. ~o, 824 Active ingredlent B D E F
kg/ha 3.0+2.03.0+2.0 3.0+2.0~.0+2.0 Cro~ plant:
; Oryza sativa 5 5 5 5 Unwanted ~lants:
..
Amaranthus retroflexus 100 80 95 Chenopodium album 100 100 100 100 Galinsoga parvlf~ora 100 100 100 100 Gallum aparine 100 80 100 90 Matrlcarla chamomilla 100 100 100 ---Polygonum persicaria 90 100 100 100 ; Sinapis arvensis 100 100 190 100 Stellaria media 100 80 100 100 O = no damage, 100 = complete destruotion.
Field weeds may be ef~ectively controlled wlth the above compounds. Rice represented Gramineae crops, and the compounds `-would appear sultable for use therein as herbicides.

l .
, In the open, various plants were treated at a growth `
helght Or from 2 to 10 cm with the following compounds:
H,,,CH~

~N'~02 -, 2 5 H," CH3 so2CH2-CH - CH3 .

: , ... .
. . .

. , .

7 ~ ~

o.Z. 30,824 H
H_,,C
L ~ N-C CH

21 ~ 1 . :
; The application rate was 1.5 k ~ ha of each compound 2 liters per hectare o~ a spreader sticker, these amounts belng dispersed or emulsified in 500 liters of water per hectare. Durlng the experlment, 9 to 11 mm of rain fell.
After ~ to 4 weeks it was a.scertained that compounds I, K and L had a strong herblcldal ~ction on dlcotyledonous plants such as Centaurea cyanus, Chenopodium album, S~napis `~l arvensls, Stellarla media, and Spergula arvensis, whereas Amaranthus retro~lexus and Polygonum perslcarla were less ;
receptive to treatment. Compounds I and L were fully ;~ compatible with Glyc~ne max., whereas compound K caused ~i slight burning and growth retardatlon in Glycine max.
I The results are given below:
Actl~e ingredient I K L
kg/ha 1.5+2.0 1.5+2.0 1.5~2.0 ,. ~ ~ ' .
Crop ~lant:
Glycine max. 0 10 0 Unwanted plants:
~ ~ .
Amaranthus retroflexus 70 40 3 Centaurea cyanus 100 100 100 . ' 1 Chenopod~um album100 100 100 ~olygonum persicaria 0 0 60 , .1 .
, Sina~is arvensis 100 90 90 r~ Stellaria media 100 100 80 Y~ Spergula arvensislO0 100 80 , . . .
; - 49 _ ,, , , ..~

~ 7~ ~
O,Z. ~0,824 O = no damage, 100 = complete destruction, In the open, various plants were treated at a growth height o~ from 2 to 10 cm with 1.0 kg/ha o~ each of the following active ingredients, each belng dispersed or emulsl~ied in 500 liters of water per hectare:

F ~ I C~-_CH~
N~S02 O=C-N~ 2C7H7n -C--CH~5 O=C-N

~I-C cH3 .' S02-NH-C3H7i .

M f~o2 Q=c-o-cH3 N ~N3-C CH3 ~; N' 2 C H
O-c-N~ 2 5 .~, C2H5 ~ loO kg/ha o~ ammonium polyacrylate was added to each spray liquor to improve the distribution of the active lngre-_ 90 _ 7 ~ ~
0,Z. ~o,824 d~ents on the surrace o~ the leaves~ During the experiment 10 to 20 mm of rain fell~
After 3 to 4 weeks it was ascertained that the compound~
; F, G, H and M had a good to very good action on the unwanted plants Chenopod~um album, Galinsoga parviflora, Matricaria chamomillaS Slnapis arvensis and Stellaria media. Compound M
also provided good control o~ Amaranthus retroflexus. Actlve lngredient N had a very good action on Amaranthus retro~lexus, Chenopodium album9 and Stellaria media, whereas the action on Galinsoga parviflora and Sinapis arvensis was not as strong.
Amaranthus retro~lexus was not, or only to a small extent, destroyed by F, G and H. Compound F was fully compatible in soybeans (Glyaine max.). Products H and G caused sllght damage to the crop plant, whereas compounds M and N damaged the crop plant to a greater extent.
The results are given below:
Active lngredlent F G H M N
kg/ha loO 1~0 1~0 1~0 1~0 `
Crop plant:
., Glyclne max. 0 20 10 45 25 Unwanted plants:
Amaranthus retroflexus 0 20 0 100 100 Chenopodlum album 90 100 95 100 100 Galinsoga parvi~lora 100 100 90 100 65 Matricaria chamomilla100 --- 100 100 ---Sinapis arvensis 85 80 90 90 75 Stellaria media 100 100 100 100 100 0 - no damage 100 = complete destructlon 7~Z
O.Z. ~o,824 These results indlcate that broadleaved weeds can be controlled with the above compounds; a suitable crop for active ingredients F, H and G is soybeans. However, this crop -is not as sultable for compounds N and especially M because of the increased amount o~ damage caused.

.: .

, .

. , ~ .

' ' .

. . .
.;, .

. . ' , .

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A substituted 2,1,3-benzothiadiazin-(4)-one-2,2-dioxide of the formula where R1 denotes isopropyl and R2 denotes a) formyl, propionyl, valeryl, sec-valeryl, capronyl, 1-(a-methylvaleryl), acyl of 8 to 16 carbon atoms, lower acyl substituted by halogen, acetoxy or alkoxy, lower acyl substituted by halophenoxy and/or alkylphenoxy, unsaturated unsubstituted acyl of 3 to 5 carbon atoms, cycloacyl of 6 to 10 carbon atoms, diacyl of 2 to 10 carbon atoms, or b) alkoxy-or alkylmercaptocarbonyl containing alkyl of 1 to 16 carbon atoms in the alkoxy group, unsubstituted or alkoxy-substituted phenoxycarbonyl, unsubstituted or halogen-substituted benzylmercaptocarbonyl, or c) unsubstituted or alkoxy-substituted dialkylcarbamoyl, dialkylthiocarbamoyl, N-phenyl-N',N'-dialkylformamidinyl, the alkyl group containing 1 to 5 carbon atoms, or d) alkylsulfonyl, containing 1 to 5 carbon atoms in the alkyl group, arylsulfonyl which may be substituted by halogen, nitro or alkyl of 1 to 5 carbon atoms, or e) mono- or dialkylsulfamoyl containing 1 to 5 carbon atoms in the alkyl group, or f) N-alkylbenzimidyl containing 1 to 5 carbon atoms in the alkyl group, or g) O,O-dialkylphosphorothioate or phosphate containing 1 to 5 carbon atoms in the alkyl group, or h) unsubstituted or perchloromethylthio, or i) phenyl substituted by nitro.