CS226433B2 - Herbicide - Google Patents

Abstract

The present invention relates to ortho (sulfonyl) oxybenzenesulfonamides and their use as herbicides. Netherlands Patent Application 121788 published September 15, 1966 compounds of formula A and their use as General or selective herbicides: R 4 and R 2 may be independently of one another alkyl having 1 to 4 carbon atoms and R 3 and R 2 'may independently represent each other hydrogen, chloro or alkyl of 1 to 4 atoms carbon. The compounds of formula B and their use as antidiabetic agents are disclosed in J. Drug. Res. 6, 123 (1974):

Description

(54) Herbicidal product

The present invention relates to ortho (sulfonyl) oxybenzenesulfonamides and their use as herbicides.

Dutch patent application 121788 published September 15, 1966 discloses the preparation of compounds of formula A and their use as general or selective herbicides:

R ₄ and R ₂ independently of each other may be alkyl of 1 to 4 carbon atoms and

R ₃ and R _Z may independently has one another represents hydrogen, chloro, or alkyl of 1 to 4 carbon atoms.

Compounds of formula B and their use as antidiabetic agents are disclosed in J. Drug. Res. 6, 123 (1974).

CL p

II

SO 4 NHGNHR (B) wherein R is pyridyl.

U.S. Patent 4,127,405 discloses compounds of Formula C

Π N

N ~ \

Y t C) where R _t is

production of these products. Preventing or reducing the loss of part of valuable crops by destroying or inhibiting the growth of unwanted vegetation is one way to improve this efficiency.

A variety of substances are available to destroy or inhibit the growth of unwanted vegetation; these are commonly referred to as herbicides. However, there is still a need for more effective herbicides that control or reduce weed growth without causing significant damage to useful crops.

The present invention relates to a novel herbicidal composition comprising, as an active ingredient, at least one compound of the general formula I wherein

R ₃ and R _c are independently hydrogen, fluoro, chloro, bromo, iodo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH ₃ S (O) _{n -} or CH ₃ CH ₂ S [O] _n -;

R ₄ is hydrogen, fluoro, chloro, bromo or methyl;

R 8 is hydrogen, fluoro, chloro, bromo, methyl or methoxy,

R ₇ is hydrogen, fluoro, chloro, bromo, C 1 -C 2 alkyl or C 1 -C 2 alkoxy;

R ₈ is hydrogen, methyl, chloro or bromo;

R ₉ and R ₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chloro, bromo, methyl, ethyl, C 1 -C 3 alkoxy, trifluoromethyl, CH ₃ S - or CH ₃ OCH ₂ - and. .

Y is methyl or methoxy; or a salt thereof suitable for agriculture, provided that, when R _{5 is} other than hydrogen, at least one of R ₃ , R ₄ , R ₆ and R ₇ is other than hydrogen and at least two of R ₆ and R 7 ₇ must be hydrogen; b) znameiná when R ₅ is hydrogen and all of R _3, R _4, R ₆ and R ₇ are other than hydrogen, then all of R _3, R _{@ 4} R @ ₆ and R ₇ must be either chlorine or methyl and cj when both R ₃ and R ₇ are hydrogen, at least one of R ₄ , R ₅ or R 8 must be hydrogen.

In particular, this patent discloses ortho-substituted compounds wherein the substituents are alkyl of 1 to 4 carbon atoms.

The presence of undesirable vegetation causes serious damage to crops, especially agricultural crops satisfying the basic nutritional needs of mankind such as soybeans, corn, wheat and the like. Population explosion and the associated global food scarcity require improved

where · means

R _{4 is} C 1 -C 4 alkyl, trifluoromethyl or a group of formula

Q is an oxygen atom or an NCH ₃ group,

R ₂ is hydrogen, chlorine or methyl,

R ₃ represents hydrogen or chlorine,

X is methyl or methoxy,

Y is hydrogen, methyl, or methoxy; and

Z is CH, CCl or nitrogen, provided that when Y is hydrogen, Z is other than nitrogen.

Advantages due to higher herbicidal activity or for easier preparation are:

1. Compounds of formula I wherein R _t is an alkyl group having 1 to 4 carbon atoms or trifluoromethyl,

2. Compounds according to claim 1, wherein R ₂ is hydrogen,

3. Compounds according to item 2, wherein R ₃ represents a hydrogen atom;

4. Compounds according to item 3, wherein R ₁ is C 1 -C 3 alkyl or trifluoromethyl, Q is O, Z is N or CH;

WITH

5. Compounds according to item 4, wherein X and Y are independently selected from the group consisting of methyl or methoxy, and R ₁ is methyl.

Particularly preferred for reasons of highest herbicidal activity and / or easiest preparation are:

N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate,

2-hydroxy-N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide methanesulfonate; and

N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate.

All of the above compounds have selective use in wheat cultivation.

N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate,

2-hydroxy-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide methanesulfonate,

N - [(4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate,

N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) (methyl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate,

N - [(4,6-dimethoxypyridin-2-yl) aminocarboinyl] -2-hydroxybenzenesulfonamide-1-propanesulfonate, having selective use in rice and maize cultivation and 2-hydroxy-N- [(4-methoxy-6) methyl-1,3,5-triazin-2-yl] aminocarbonyl] benzenesulfonamide 1-propanesulfonate, which has selective use in growing soybeans.

The present invention also relates to compounds of formula (II) which are useful intermediates for the preparation of compounds of formula (I):

where it means

Q is O or NCH ₃ R _1, C 1 -C 4 alkyl or trifluoromethyl or formula

β

R ₂ is hydrogen, chlorine or methyl,

R ₃ is hydrogen or chlorine.

Preferred intermediates for ease of preparation and / or higher herbicidal activity of the compounds of Formula I are:

1. compounds of formula (II) wherein R @ ₂ and R @ ₃ are each hydrogen, R @ 1 is methyl or trifluoromethyl and Q is oxygen;

2. Compounds of formula II where Q dizzy group of formula _NCH3, R ₂ and R ₃ are hydrogen and R _t a methyl group or a trifluoromethyl group.

The present invention also relates to compounds of formula (VII) which are useful intermediates for the preparation of herbicidally active compounds of formula (I).

where

Q is O or NR ₅ ,

R _f is C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with 1 to 3 F, Cl or Br atoms, CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ CH ₂ OCH _3, or a group

R ₂ is H, F, Cl, Br, OCH _3, NO ₂ or alkyl having 1-2 C atoms,

R ₃ is H, F, Cl, Br or OCH ₃ ,

R ₅ is C 1 -C 4 alkyl,

R ₆ and R ₇ are independently H, F, Cl, Br, CH ₃ , CF ₃ , NO ₂ or OCH _3, and

Z is CH or N.

The compounds of the invention may be prepared as follows. Compounds of formulas IV, VI, XII or XIV may be prepared by reacting a suitable 2-aminopyrimidine, 2-aminotriazinium or 2-aminobicyclopyrimidime of formulas III, V, XI or XIII with an appropriately substituted sulfomylisocyanate or isothiocyanate of formula II wherein Q, R _{1 (} R _2, R _3, R _4i X, Y, Z, X _{1 (X 2,} Y _{1 (Y 2,} W and n are as defined above.

This reaction is preferably carried out in an inert solvent such as methylene chloride and acetonitrile. The addition process is not essential, but it is often convenient to add a solution of isocyanate or isothiocyanate of formula II to a stirred aminoheterocycle suspension of formula III, v, XI or XIII.

This reaction is generally exothermic. In some cases, the desired product is insoluble in the reaction medium and crystallizes therefrom in pure form. The reaction-soluble products are isolated by evaporation of the solvent and trituration of the residue with solvents such as di-ethyl ether, 1-chlorobutane or hexanes and filtration.

IV

and.

II

X

R

Η- γ

II

III

3.

//

In the above formulas and in the possible subsequent general formulas, the individual symbols have the meanings given above and W represents the science of oxygen.

The compounds of the invention may also be prepared by reaction of a sulfonamide of formula

VIII with a 4,6-dichlorheterocyclic isocyanate of formula IX.

4.

Ct ct

NCO (IX)

One or both of the halogen atoms on the heterocyclic ring may be replaced in the compound of formula (VII) by an alkoxy OR ₈ to give compounds of the formula X wherein R ₈ is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, alkenyl. C 3 -C 4, CH ₂ CH ₂ OCH 3, or C 2 -C 4 alkyl substituted with 1 to 3 F, Cl or Br, and Y "is Cl or OCH ₃ .

w <1 ct

S0.NHGNW- / O

N- <

(VII)

Whose

VIIaso / _0R

OT O Nr-S

SO, NNGNM- (Oz

Na> OR _&

Ν—

The sulfonamides, which are prepared as described in Research Disclosure, p. 52 (1978), can be conveniently converted to the corresponding isocyanates or isothiocyanates of formula II by the methods described in US Patent 4,127,405.

Syntheses of heterocyclic amine derivatives have been reviewed in "The Chemistry of Heterocyclic Compounds", in a series published by Interscience Publ., New York and London.

2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series.

The preparation of aminotrcyclopyrimidines is described in European Patent 15,683, published without examination.

Aminoheterocyclic intermediates of formula (III), (V), (XI) or (XII) wherein R ₄ is CH ₃ may be prepared by the following procedure

H _£ NCH ₃

NA cnjnn- ^ Qz * 3 NA Y

A solution of the amine of formula XV in concentrated hydrochloric acid is contacted with an aqueous solution of sodium nitrite and is isolated from the acid medium by filtration with chloro-compounds of formula XVI [see, e.g., Bee and Rose, J. Chem. Soc. C 2051 (1966)] for the case where Z is CH and X and Y are OCH 3. Chlorine exchange can be accomplished by heating with an excess of mothylamine in water to form a methylamino-heterocycle of formula (XVII).

N-Methoxyaminoheterocycles can be prepared by methods known in the literature [see, e.g., Belgian Patent 618,563 and J. T. Shaw et al., J. Org. Chem., 27, 4054 (1962)] and the procedure illustrated below.

λ \ n N '/ d / N

Y (XVI)

X > -N (OH) -N

Y (XVIII)

X / zN + CH ^ Br - ^ z ^ j / NHOCH 2 ^Y (XIX)

XVI 4- N ^ OCH ^ HCt XIX (XVII)

221)

The chloro compound of formula (XVI) is reacted with hydroxylamine to form a derivative of formula (XVIII) which can be alkylated with methyl bromide to form the N-methoxy-heterocyclic amine of formula (XIX). Alternatively, this compound can be prepared in one step by reacting a compound of Formula XVI with O-methylhydroxylamine hydrochloride and an alkali metal hydroxide, such as sodium hydroxide.

The compounds of the invention and their preparation are further exemplified by the following examples wherein the temperatures are in degrees Celsius and parts are parts by weight unless otherwise indicated.

Example 1

2-Hydroxybenzenesulfonyl isocyanate methanesulfonate

To 10.0 g (0.04 mol) of 2-hydroxybenzenesulfonamide methanesulfonate suspended in 75 ml of anhydrous xylenes are added 4,0 g (0,04 mol) of N-butyl isocyanate and a catalytic amount of 1,4-diazobicyclo [2.2.2] octane (about 0.05 g). This mixture was rapidly heated to reflux (~ 135 ° C) and 4.0 mL of phosgene was added slowly (at a rate such that the temperature of the reaction mixture was above 128 ° C). Addition of phosgein is completed in about 11/2 hours. The reaction mixture was cooled to room temperature, filtered under nitrogen and the solution was evaporated under reduced pressure. The infrared spectrum of the resulting oil corresponds to 2-hydroxybenzenesulfonyl isocyanate methanesulfonate (2210 cm ^-1 ).

Example 1 a d 2

N - [(4,6-Dimethoxypyrimidin-2-yl) anionicarbonyl] -2-hydroxybenzenesulfonamide methahsulfonate

To a suspension of 0.5 g of 2-amino-4,6-dimethoxypyrimidine in 10 ml of anhydrous methylene chloride was added 1.1 g of 2-hydroxybenzenesulfonyl isocyanate methanesulfonate. The reaction is exothermic (21 ° C - 29 ° C), then stirred for 1/2 hour. The solvent was evaporated under reduced pressure. The resulting mixture was triturated with diethyl ether and filtered. It arises

1.2 g of a tan solid, m.p.

165-166 ° C. The infrared spectrum shows absorption at 1740, 1615, 1590, 1360 cm ^-1 . Calculated:

% C, 38.9;% H, 3.73;% N, 12.9; Found:

38.3%! H, 3.63; N, 13.0. Example 3

2-Hydroxy-N- [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide methanesulfonate

To a suspension of 0.6 g of 2-amino-4-methoxy-6-methylpyrimidine in 10 ml of anhydrous meithylein chloride was added 1.1 g of 2-hydroxybenzenesulfonyl isocyanate methanesulfonate.

The reaction is slightly exothermic. Then stir for 1/2 hour. The solvent was evaporated under reduced pressure. The resulting mixture was triturated with diethyl ether and filtered to give 0.95 g of a white solid, m.p. 189-190 ° C. The infrared spectrum shows absorption at 1700, 1615, 1560, 1370 cm ^-1 .

Calculated:

H, 3.87; N, 13.4. Found:

H, 3.77; N, 13.6. Example 4

N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate

To a suspension of 0.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 10 ml of anhydrous methylene chloride was added 1.1 g of 2-hydroxyphosphoric sulfonyl isocyanate methanesulfonate. The reaction is slightly exothermic. Then stir for about 1 hour. The solvent was evaporated under reduced pressure. The resulting mixture was triturated with diethyl ether and filtered to give 1.4 g of a tan solid, mp 163-166 ° C. The infrared spectrum shows absorption at 1715, 1600, 1550, 1350 cm ^-1 .

Using procedures similar to those described in Examples 1-4, the following compounds can be prepared.

2 G 4 3 3

CD O vo CD OO CM CT> CD O? O CD 00 CD i — 1 rH 1 T ~ Í CM AND τ — 1 AND i — i rH AND rH | CM 1 1 in O) 1 TJ1 1 00 O 1 tH 1 what 1 CD what 00 O what > p 00 vo rH rH i — 1 CM rH rH i — l r ~ ( CM

tr «ηη Η · 4 wh * T7 · KH eo co eo eo eo tii eo eo • τ 'co oo> * ri hh hh er> -L- | HRH-f r4 | -M L-Hpl pl | H PH M t H ^u ouSu3 ^ouu "

O ^uo OCO> 1 eo eo eo eo eoeOeO co wh> τ · eo> t <tr · * eo hr * * t <* t * 'Χ'ί-Ι-ΙΙ-ΗμίΗμίΗ'Τ'Η-ΙΗΗΗ-Ι

00 ^ 00 ^ 000 o oo oo ^{u u} ooo of eo

E

O o

² Y ^and ooooooooo o

Table

Pi ooooooooo o

M HH hH H>) tH HH? H M-Γ t ⁴ * T * hr · ►t * T * »* T * T * T * T * HH *» τ · **! ·

Η ^ μΗΗ-ΐΗΗΚ ^ ΗΜΗΗιΧίΗ-) ρΧρ to

EEEEEEEEE ffi «ω E E>

Γ3 w-i?

()Ο) · ϊ'1

X!

řH

Fri «

honors c

Pi

Who knows>

-tfi

Η

HM Krt HM HM HM HM hH HiM oooooooooo? O c * «rt w« rt

HM HM HM HM HM HM HM * M μΧΗΗΜΗΜΗΜΗΜΗΜΗΜΗΜ oooooooo

and and and and and O O O O O O O O O O

rtrtrtrtrtrtrtrtrt

HM HM HM Hrt HM HM HM t ^ l HM l_H HM HM HM Hl HM | _Lm) _Lm KH ooooooooo ooooooooo ooooooooo

OOOOOOOOO aaaaaaaaa

aaaaaaa ^ u xjl i

5P

aaaaaaaaa

000O00000

CD

CO and tC * -7, zEj L1. a * 5 * _{2 2} a aam ř u: z: z _from aaaa ^^ OOOu ^ On ^^^ OOOO a «a” r aaS ^^ a

HM ¹ ^ ffi XX uaogaa * ° EOoog ι! II o cq eoHM _£ C, "go S & S» ri a 'T! ^ Cj Λ o I ^ Um

Ξ, ι I ou

Cl a

o o and o

O

E

-cj aga and ⁵

O O «ϋ what what lij m o HM <—> m« Μ «Η« «« Η COhm «A 7ia« aasaíaaaíaí a ^ gggggogggogo

O o o o c o e o and X o o o o o o cOCOCOCOCOSOCOCOCOCO

Μ HH HM HM HM HM HM HM HM _r <i> JMHMHMI-1MHMHHHMklMHM HM guuuuuuuuuu η M what what COCOCOCOCOCOCOCO rtH HM CO HM HM HH ημμμηιηιηηη-iUU ^ ^ hAAhh Χ

OOOOOOOOOggOgoUo oo o oooooooooooooo o

O OO O OO OOO w w Wcntnwo g — g oooooooooooooo o

OOOOOOOOOOOOOOOOOO

Honors

HM HM HM HM HM HM HM MM HM HM M HM

UmmAAAAAAAAAA HM

HM HM HM HM HM HM HM HM HM HM HM MM MM Um UmMaMiMaTiMaTiMaTiMeMiMiM

BB B

HM HM HM HM HM HM HM HM HM HM Um Um Um Um Um Um Um HM Um Um HM HM

M HM HM HM HM HM * T * Η * Η ⁴ Τ ⁴ * T * Η ¹ * T * Η ⁴ Η * UmhM> MMHMHMHmUmUmUmUmUmUmUmUmUmUm

M HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM

A MM Um UmmUmUmUmUmHmUmUmUmUm HM Um UmUmUmUmUmUmUmUmUmUmUmUmUmUm I

WHAT

What what coeococococoeocococococo co hm ΗΗ HM Η ⁴ Η ¹ HM HM H ⁴ HH Η ⁴ η * Η ** Η ⁴ * Ή Η ⁴ Η ⁴

Um Um Um Um Um Um Um Um Um Um Um Um Um Um Um

OO O OOOOOOOOOOOO by cococococococococo-ocococoeocococo

UUiHiHiUUHMiT * AAAAh-iAAA Um Um Um Um Um Um Um Um Um Um Um Um Um Um Um

OOOOOOOOOOOOOOOOOO in co

rH OJ what OJ CO CO., LTD O xři CO TP 0- O rH of-\  - ' 05 / WHAT 05 / o in co l> 00 ao 05 / WHAT i-M r — 1 τ — 1 rd rH OJ r-1 r 'i Ή rH tH tH rH rH rH Λ N O O N 1 1 1 1 1 1 1 1 1 1 1 1 1 O OJ O O) O CD HO H 1Ω OJ CO OJ XJ1 in 05 / Jm Fm 00 WHAT 05 / o in co CO t> 00 oo 00 OJ -—> rH t-H rH OJ rH rH τ — 1 tH τ — i tH tH tH rH

uooo ^ yoo o ffi SS £ o o o ω ω o es n

PS

PS cc

Prd «P * H ph ogo ^u

CO ffi

O

O

OO M xtc κ o o o wO, .o

HM | ..... ..

in in

CO CO CO CO

HM HM CO CO HM HM CO CO hm.

ΓΊ Γ 5 wt Hh hH r λ w Hh Γ Ί oo ^{uu uuu} about what what · · · CO as the CO

HM CO CO HM. CO CO HM CO CO HM

Γ 0 HM HM HM HM H Γ> HM HM no ^uu ° about the ^{Y u} · ° what what what what i M CO CO CO Co Co HM HM HM googcuugoog CO CO Co Co Co Co Co Co; HM WHAT WHAT WHAT WHAT WHAT HM WHAT HMHM WHAT iJ-iHmhmjJhhmhmhMhmhUhUhMhm gSSgSSgggggS what what what what what what what what what what what what what what what what what what

HM HM HM · COHM-HM HM CO HM HM CO HM HM OHH.HM · CO. HM-.HM. HM HM HM HM HM HM HM HM HMU HM HMU HM HMU HM HMU HM HM: HM HM j-Im. HM ^ -, ηΜΜ-ι. hmhUiJmhmhMhmhMhMhJhhM .oooSuouíuogooftuu «* oo« * ooSu uouu ooo ooo ^{u u u} oo oo oo ^{u u u} oo oo ^u ooooo

O O O O O O O O O O O O 0-00 0 0 0-0 0 o o o o o o o ffi o.

CS R «« ^m by "Pt; íč 3 3-3'θ oooo oo o oo ooo oo oooooooooo Sgzzz ^from £

CO-HM. HM..HM..HM. HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM HM

U O O μημμμμΜΜΜΜΜΜΗΜΜΜΜΜΙΜΜΜΜΜΙΜΗηΜΜΜΜΜΜΜ i i i hmhmhmhmhmhmhmhmhmhmhmhmhmhmhm hm hmhmhmhMhmhmhmhmhmhmhmhm hm hm what what what what about

Co Co cOcocococococOcococococococo f tC ϋ """""""and ffi ffi weex IX EX-SC to the IC Κ CQ pff oo ^ p ^ gggggggooooo ££ £ £ d κ ίέο 5 □ □□ OQUOSSUUUOĎĎUOUUĎU pg ^g-1" 'u

Pí n

Pi

Pi

MH MX | -L | H ΜΗ ΜΗ ΜΗ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ ΣΡ

MH? WHAT M * P "'_« ^ i £ R £ sg, 1¾% síg5§É8šS5 Ξ ^ g £ Z = »oox X 2 c X ^u u · cj

ZzgggSusgSSíiÍK'goggffO CO CO t-r * T

ΜΗ HH MM · ~ * Η r-H r — I * CJ CJ CJ CJ CJ

CJ cOfOCOeOcOCOCOíOíOeOCO μμμημμμημημμμημμμμμημμ MM mM MH MH MH MH MH MH

CJCJCJCJCJCJCJCJCJCJCJ ooooooooooooooooo ac ac ac xxx _of acxcjo yx uo by cj cj oo O CC ouo "3? ac ac of cj acgoo ^^ ^u o O OJ? ^ 0 £ Μ ιΐι render me «Ο COMH MH MW ^ g ^ ogg oggggg ^u c ^u ooo cj® xacxx oy cj cj cj ° about oooo

CO CO CO «0 CO co acxxxxxac

CJ CJ CJ CJ CJ CJ10 00 ~ xxx

CJ CJ CJ CJ COO COO COO COO COO COO COO COO COO COO COO COO COO COO COO COO

ΜΗ ΜΗ MHMHMHMHMHMHMHMHMH MM MH MH MH MH MM MM MM MM MH

MH MM MH MM MM MM MM MM MM MH

MM MM MM MM MH MM MM MM MM HH

MM MM MM MM MM MM MM MM MM MM MM MM MM MM MM MM HH MM MM MH MM MH MH MH MH MH

Ι ^ ΜΜΜΜΙΜΗΗΗΗΗΗΗΜ MH ΜΜΜΜΙΜΗΗΗΗΗΗΗΜ ΜΜΜΜΙΜΗΗΗΗΗΗΗΜ MH MH MH «« «« «« «« «

XX cj «1 cj cj o« X oo x> WHAT WHAT WHAT WHAT? «0« 0 w «<ν4ηΜΗΜημηΜηΟ • τ '►Τ' MH mm μη μη μη« V * μημη _γ ^ ηΙημΙημΙημη μΙημΙημΙημημΙημμμμμμη ⁰⁵ g 5 «CJ CJ CJ CJ X> Ό J CJ CJ ο cofocoeocococococococoío

MM ΜΗ ΜΗ ΜΗ ΜΗ ΜΗ ΜΗ ΜΗ ΜΜ ΜΗ ΜΜΗΗΜΗΗΜΜΗΜΗΜΜΜΜΜηΜη ΜΗ

CJCJC3OCJCJCJCJCJCJCJ

220433

rH ID WHAT b * r * 4 OO WHAT rH τ — 1 CD what WHAT WHAT CM ID ID 03 / O 00 00 rH 00 00 WHAT 00 WHAT CM 00 00 05 / rH 1 CM AND tH 1 r-1 1 CM 1 rH AND r-H τ — f AND Ή 1 tH | r — 1 AND CM ( τ — 1 | t-H | τ — 1 1 τ — l AND rH 1 1 05 / 1 ”Φ 1 0 1 rfi 1 O l τ— < rH l 0 1 05 / and WHAT 1 what 1 τ — 1 1 CM 1 1 05 / 1 what 1 what frs 0 what 00 rH 00 00 ID tx what CM 00 00 WHAT 05 / τ — 1 CM iH tH CM tH rH τ — 1 rH rH rH CM tH rH tH rH τ — 1

ΧΧ _ΖΖ θΧΧΧ _ΖΖΖΖ Χ

CQ CQ <73 _ CO

CO co t-rt CO co t-r <co co * r <COHH co

Η * 'Τ ¹ <-H * -Γ <<77 * · - r <~ <73 7- (JL, h-3 <.π ri cL · c ^ r' 1 ^J , π- η τ * ¹ r Ί - * uoguogooogugu _of XX 4 00

X X X 0 u o 0 0 0

what

X co. . ? X X,

X X XPX X X hU rvi co

X X yKuGKub ^ ocirtOO

* Ί ^w * - '> r * \ oo ^u 00 ^u oo fO

X o

About what

X X o o o o

0000000000000 o

00000000 00 000 ί ¹ honor

XXXXXKXEEKKgK ffi

X ⁵ X g Sx honors

-Η-ΙΗ-'Η ^ ΜμΗΙτΗΗι-Ι K-t hlM

hh | 4h h-i Ph hJ-1 HM hh HH H-t hM HH l-H hi-1 (Jh

X XX honors eo. m what -Λ what what what what

X

F - If - »(- if - li - MKrt i - HI - I - 1 Hill - jHHHHjHU □ O □ B O Λ HH hL> i | μΙ - I (Jh Uh ^ 5.

ΎΎΎΎΎ0000000Χ iniflinifliD i 1 '· <«rd lldidldldldldldCj i

X XX cocococococococococococoeoco

MMI-Kt-MHM1-Llt-MH-IHMI-H11-IHMI-HHH

OOOyQQOyQyOOU

> <

CT> T! ^1-1 Pc I n IS °

H 05

Pi

N o

(η

P I P <£ NN ^N ř 4 4 P- <

Z22 2

HH fO M

Xx o ^uo co

X o

m

X

O

O

M «

XX o o oo <0 rt

X X o o o o «

X u

o w

X u

o m

X u

O

OCH o o ooo o o * 0 «0. CO Ot CO CO W

Ř r »» »* * * * * 4 4 4 4 4 4» »4» »» »» »» »» »» 4 »» 4 4 cg— _ο 2: —ο 2 — ο 2 — ο 2 — ο 2 — ο 2 — ο

Ptí

X! XXX X X X

Pi

Μ Μ br * ΗΜ Μ Η “* * Τ *

4-4 4η 4μ 4η 4η 4η 4-t 4 *

Pi

P1 χχχχχχχ X X X X X X

Ů0 Λ Λ XX fa u yuu _r «

X

Ο «ί

X

Ο &?

ο

Γ ^Λ

X ο

t £ ο

H ri T-N N N M r Hr 1 Hr 1 NH-IH-co co

CO H | M WH HM HM

KKgffiggg ° for ^u xj ^ oo £ χ χ x * u * ^u u§ooo by ^u o ^u ooo <M 5N ooggoooo about oooooooo

Fri «

oi

OOOOOO ^ _gOQOOOOOO o .M HM HM HM-HH HM hm hm hm mm hm mm hm

HM HM HM HM HM HM HM MM HM HM HM HM HM

HH M hH M ¥

MM HM HM HM HM HM ffi X X X X 33 as ffi x ffiXXXXXXX χ

OOUOOOws ffi

I 1 I <| | HH HM Um ini in in in in

Table II WHAT WHAT WHAT WHAT WHAT WHAT

HM HM HM HM HM MM HM

MM MM MM MM MM MM

O u u o o o

ČOhM ^KU "OH? WHAT MM WHAT WHAT WHAT WHAT EO / - ^ ri

X X X X X X OOOQOU * ^

Ε, κ

I O

• s <

Pi

Pi

5 ’

Pi

Pi

CM

CM what what

X X

OO J .. ~ - - - - οο '-' οοοοο co oo what eo « ^: Χ KX χ X uoooo oooooooo τ— | rH γΗ, Ή rt τ-Η τ — IC \ J rf, CM

CO CO CO CO CO CO ® tc £ χ χ χ xg 5 c goQUOUCg ^UU

000 ^ 000 ^ 00 o

OOOOOOOO O tnc / iOOOOOOOO

CO I co ooooooooooooooo oooo κχχχχχχχχ χ xxggaaSaxx '-γ · ^, τ · * τ ¹ »τ ⁴ * τ · ^ -) ^, τ · ^> τ * hm hm hm hm mh i hm hm co

XXXX ^^ UX

u) ^UJ co —I

X ο o ω rj) <nc ^ i C4 * τ · Μ hrt CO what what ^ hM iL (LM hh r r r r> hm h> h mh hm + + + Cc OO axis XXX κxxax χ χ xsa xxxxxxxxxx what what what what

CO CO CO CO CO - - ^ 4

000 m "m κ» _ "m

KfC HM hr. * 5 PS hrl -rl 4-, hL, kpi i-pt Uh

MM CO Μ Μ M

Hpl HŠ p1-1 PiH HH M

PH PH PH PH PH pU | ooo ooo oooooo eo what what what _- what

MM Μ Λ Μ CO M J H and 4H Uh »T * ω Uh about rt oo oooo u ^uu what what what what what what

M M Μ Μ Μ M

Μ PM M PM PH PH

O o u o ϋ o oo o ooo

OOwOOOO oo

OOO eo

OOOOOOoO O OOO

& EEEgEgE

Pi

⁵

ΕΚ E KEo

O

EKEESEE EE E? o E «**

Qc

Pi

M Μ Μ Μ M M «M

Ppf Μ Μ Μ Μ Μ M

HM beep pL (hH PH PH HM

O O O O O ϋ o

Table III eo co ffo _ eo

E w? EX s? EE uftuo ^ Su what what what what what <<he on what what he oL, oW OH oU WH he oIh oooo «S o oooo ^uu o

OOOOOO what what what what what what

OjH WH Fil W Wl W

CH HH W HH oW OW

O O O DUO

OO o ooo what what what what what

ESC ffi ffi K

O o o o o o o o o o

-5 o o o ooo

Table IV

tca en tese®

EEEKKKE

Effi E XK5 O.

Effi E EEE

Pi

5 Λ Λ Λ CT5 5

HH KH t-M Hr1 Hp-t-M W-t

M- (> X * Mh bW t-MΜ-i HM

O O O O O O O

Resources

Useful compositions containing the compounds of the formula I according to the invention can be prepared by conventional methods. They include powders, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these agents can be applied directly. The spray compositions can be dispersed in a suitable environment and used in a spray rate of several liters to several hundred liters per hectare.

Compositions with a high concentration of active ingredient are primarily used as intermediates for the preparation of other compositions. These compositions contain, in a broad sense, about 0.1 why. up to 99% by weight of the active ingredient (s) and at least one of the aj surfactants and, (b) a solid or liquid diluent (aj in an amount of about 1% to 99%). More specifically, the compositions comprise said agents in the following approximate ratios:

Table V weight percent * active ingredient diluent (also surfactant (s)

wettable powders 20—90 0—74 1—10 oil suspensions 3—50 40—95 0—15 emulsions, solutions (including emulsifiable concentrates) aqueous suspensions 10—50 40—84 1-20 pills 1—25 70—99 0-5 granules and pellets 0,1—95 5—99.9 0—15 highly effective means 90—99 0—10 0—2

* The sum of the weight percent of active ingredient and at least one surfactant or diluent is equal to 100 weight percent.

However, higher or lower levels of the active ingredient may be employed depending upon the intended use and the physical properties of the compound. Sometimes higher surfactant to active agent ratios are desirable and can be achieved by incorporation into the formulation or by mixing in a tank.

Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either natural or synthetic, may be used. Diluents with higher absorption are suitable for wettable powders and higher density solvents for powders. Typical liquid diluents and solvents are described in Marsden's "Solvents Guide", 2nd Edition, Interscience, New York, 1950. Solubility below 0.1% is suitable for suspension concentrates; the concentrates in solution are preferably stabilized against phase separation at 0 ° C. Surfactants and their suitable uses are disclosed in "Mc Cutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, NJ Jersey, and Sisely and Wood, "Encyclopedia of Surface Active Agents," Chemical Publishing Co., Inc., New York, 1964. All compositions may contain minor amounts of foaming, sintering, corrosion, microbial growth, etc. additives.

Methods for preparing such compositions are well known. Solutions are prepared by simply mixing the individual components. Fine solid compositions are prepared by mixing the ingredients and usually by hammer mill or fluid bed milling. The suspension is prepared by wet grinding (see, e.g., Litttler, U.S. Patent 3,060,084). Granules and pellets can be prepared by spraying the active ingredient on a preformed granulate or by agglomeration methods. See J. E. Brownlng, "Agglomeration", Chemical Engineering, December 4, 1967, p. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Edition McGraw-Hill, New York, 1973, pp. 8-57ff.

Further data relating to this field can be found, for example, in the following literature:

Η. M. Loux, U.S. Patent 3,235,361, Feb. 15, 1966, col. 6, line 16 to col. 7, line 19 and examples 10 to 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192,

14 March 1967, col. 5, 3. 43 to col. 7, line 62 and examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Patent 2,889,555, June 23, 1959, col. 3, line 66 to col. 5, line 17 and examples 1-4;

Klingman, G. C., &quot; Weed Control as a Science &quot;, John Wiley &amp; Sons, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101 to 103.

In the following examples, all parts are by weight unless otherwise indicated.

nBU3

1S

Example 5

Wettable powder

Sodium N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfanamide methanesulfonate 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2 ° / o synthetic amorphous silica gel 3% kaolinite 13%

The components are mixed, ground in a hammer. until the particle size is substantially below 50 μχα and the mixture is mixed again.

Example 6

Wettable powder

2-hydroxy-N- ((? -Methoxy-O-methyl pyrimidin-2-yl) Jamtoocarbonyl) benzenesulfooamld-methanesulfonate 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomic clay 46%

The components are mixed, coarsely ground in a hammer mill, and the final particle size, substantially below 10 μπι in diameter, is achieved by grinding with an air stream. The product is mixed again before packaging.

Example 7

Granule

Wettable Powder of Example 6 5% Attapulgite Granules 95% (U.S. S. 24-40 mesh; 0.84-0.42 mm)

A wettable powder suspension containing 25% solids is sprayed onto attapulgite granules in a two-cone mixer. The granules are dried and adjusted.

Example 8

Extruded pellets 2-hydroxy-N - [(4-methoxy-6-methyl-1,3,5-itriazin-2-yl) amino] carbonyl} -benzenesulfonamide methanesulfanate 25% anhydrous sodium sulfate 10% crude calcium ligntasulfonate 5% sodium alkylnaphthalenesulfonate 1% 'calcium / miagnesium bentonite 59%

The ingredients are mixed, ground in a hammer mill and then moistened with about 12% water. This mixture is then extruded into cylinders of about 3 mm diameter, which are cut into pellets of about. 3 millimeters long. These pellets can be used directly after drying, or the dried pellets can be crushed to pass through a No. 20 sieve (0.84 mm aperture). Genetic particles captured on US No. 40 mesh (0.42 mm holes) can be used to adjoin the array and the finer particles return to the cycle.

Example 9

Oil suspension

N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate 25% polyoxyethylene & orbitol hexaoleate 5% higher aliphatic hydrocarbon oil 70%

The components are comminuted in a sand mill until the particle sizes are reduced to below about 5 µm. The resulting thick suspension can be applied directly, but is preferably applied after undiluting with oil or emulsifying in water.

Example 10

Wettable powder

Sodium N - [(4,6-dinethoxy-1,3,5-phiazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate 20% sodium alkylniaphitalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methylleelulose 3% attapulgit 69 %

Mix the ingredients thoroughly. After grinding in a hammer mill and reaching substantially all particles below 100 μτα, the mixture is again mixed and sieved through a No. 50 sieve (0.3 mm aperture) and adjuvanted.

Example 11

Granules of low active substance concentration

N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) (methyl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate 1%

N, N-dimethylforBitamide 9% attapulgite granules 90% (U. S. S. 20-40 sieve)

The active substance is dissolved in a solvent and the solution is sprayed onto the dust-free granules in a double-cone mixer. After spraying, the granules are mixed for a short time and then adjusted.

Example 12

aqueous solution

N- [(4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -4-hydroxybenzenesulfonate methanesulfonate 40% polyacrylic acid thickener 0.3% dodecylphenol-polyethylene glycol ether 0.5% disodium phosphate 1 % monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%

The ingredients are mixed and ground together in a sand mill until all particles reach a particle size below 5 μΐη.

Example 1 d

Solution

N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfomate, sodium salt 5% water 95%

This salt is added directly to the water and stirred until a solution is formed which can then be adjusted for use.

Example 14

Granules of low concentration of active ingredient

2-Hydroxy-N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide methanesulfonate 0.1% 99.9% by weight aptapulgite granules (U. S. S. 20-40 mesh)

The active ingredient is dissolved in the solvent and the solution is sprayed onto the dust-free granules in a double-cone mixer. Upon completion of the feed, the granules are heated to remove the solvent by evaporation. The granules are then allowed to cool and adjusted.

Example 15

Granule

N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate 80% wetting agent 1% crude lignin sulfoinate salt (containing 5-20% natural sugars) 10% attapulgite clay 9 ° / O

The ingredients are mixed and ground to pass through a 100 mesh screen. This mixture is introduced into the granulate in the fluidized bed, the air stream is added so that the mixture is slightly fluidized and the fluidized material is sprayed with water. Fluidization and spraying are continued until granules of the desired size are formed. The spraying is then terminated, but the fluidization is continued, optionally with heating, until the water content is reduced to the desired value, generally less than 1%. The granules are then removed, sieved to the desired size, generally 1410-149 µm, and adjusted for use.

Example 16

Highly effective concentrate

N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) amimocarbonyl] -2-hydroxybenzenesulfonamide methanesulfoinate 99% silica gel 0.5% synthetic amorphous silica 0.5%

The ingredients are mixed and ground in a hammer mill until a mixture is formed which essentially passes through a No. 50 mesh U.S. sieve (0.3 mm holes). This concentrate may be further treated if necessary.

Example 17

Wettable powder

Sodium 2-hydroxy-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide methainsulfonate 90% dlocltylsulfosuccinate sodium 0.1% synthetic fine silica gel 9.9%

The ingredients are mixed, ground in a hammer mill until substantially all particles are below 100 µm. The mixture is then sieved through a US 50 sieve and adjusted.

Example 18

Wettable powder

N - [(4,6-Dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate 40% Sodium ligninsulfonate 20% Montmorillonite clay 40%

The ingredients are thoroughly mixed, coarsely ground in a hammer mill, and then further comminuted in an air stream until substantially all particles below 10 μπι are formed. The mixture is then mixed again and adjusted.

Example 19

Oil suspension

2-hydroxy-N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide-1-propanesulfonate 35% blend of polyalcohol esters and carboxylic acids and oily soluble petroleum sulfonates 6 % xylene 59%

The ingredients are mixed and milled together in a sand mill until substantially all particles are below 5 μτη. This product can be used directly, after dilution with oil or after emulsification in water.

Example 20

Powder

N - [(4,6-dimethoxypyrimidin-2-yl) aminocarboxynyl] -2-hydroxy-oxyphenenesulfonamide-1-propanesulfonate 10% and 10% pyrophyllite 80%

The active ingredient is mixed with attapulgite, ground in a hammer mill to substantially all particles below 200 μπι. This concentrate is then mixed with the dusted pyrophyllite until a homogeneous mixture is obtained.

The compounds of the invention are potent herbicides. They are suitable for pre- or post-emergence weed control in a wide range of areas where complete control of all vegetation is desirable, as well as around fuel tanks, ammunition depots, industrial storage areas, oil wells, natural theaters, billboards , on road and rail networks. By properly selecting the dose, period and method of application, the compounds of the invention can be used to influence beneficial plant growth as well as selectively control weeds in crops such as wheat, barley, rice, corn and soybeans.

The exact amount of the compound of formula I to be used in the present case varies according to the desired final effect, the degree of foliage, the weed species, the crop type, the soil type, the composition used and the method of application, climatic conditions etc. it cannot be prescribed for all situations. In a broader sense, the compounds of the invention are used at rates of about 0.001 to 20 kg / ha, preferably in the range of 0.01 to 10 kg / ha. Generally, higher rates of application of the above range are used under unfavorable conditions or where prolongation of soil action is desired.

The compounds of formula I may be combined with other herbicides and particularly suitably combined with ureas such as 3- (3,4-dichlorophenyl) -1,1-dimethylurea (diuron);

triazines such as 2-chloro-4- (eithylamino) -6- (isopropylamino) -s-triazine (atrazini);

uracils such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil);

N- (phosphonomethyl) glycine (glyphosate);

3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4- (1H, 3H) -dione (hexazinone);

N, N-dimethyl-2,2-diphenylaicetamide (diphenamide J;

2,4-di'Chlorophenoxyacetic acid (2,4-D) (and closely related compounds);

4-chloro-2-butynyl-3-chlorophenylcarbamate (harbanj;

5- (2,3-dichloroallyl) -diisopropylthiocarbamate (diallat);

M

S- [2,3,3-Trichloroallyl] diisopropylthiocarbamate (trilate);

1,2-dimethyl-3,5-diphenyl-1 H -pyrazolium methylsulfate (difenzoquate methylsulfate);

methyl 2- [4- (2,4-dichlorophenoxy} phenoxy] propanoate (diclofop methyl);

4-amino-6-tert-butyl-3- (methylthio) -1,2,4-triazin-5 (4H) -one (metribuzin);

3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea (linuronj;

3-isopropyl-1H-2,1,3-benzothiodiazin-4 (3H) -one-Z-2-dioxide (bentazone);

N-trifluoro-N, N-dinitro-N, N-dipropyl-p-toluidine (triflunailin;

1 H -dimethyl-β-bipyridinium ion (paraqualt);

monosodium methanarsonan (MSMA);

2-chloro-2 ', 6'-diethyl (methoxymethyl) acetainilide (alachlor};

1,1-dimethyl-3- (α, α, α-trifluoro-m-tolyl) -urea (fluometuron); and

5- [2-chloro-4 - {(trifluoromethyl} phenoxy] -2-nitrobenzoic acid in the form of methyl ether (acifluoromethylmethylene);

The potency of these compounds was determined by greenhouse testing. These tests are described and the results are given below.

Test A

Seeds of dew (Digharia spp.j), hedgehogs (Echimochloa crusgallij, deaf oats (Avena faitua), Cassie (Cassia torah), mulch (Ipomoea sp.J, beet (Xanthium ssp.j), sorghum, maize, soybeans, rice, wheat and tubers (Cyperus rotundus) were planted into the culture medium and treated preemergently with a solution of the compounds listed in Table A dissolved in a non-toxic plant solvent. leaves (including uterine, truncated bean with three-leaf triple leaf, dew and hedgehog with two leaves, deaf oats with two leaves, Qassia with three leaves (including uterine, bladder, and four-leaf beet (including uterine, sorghum and maize) four strips, soybeans with two cotyledons, rice with three leaves, wheat with one leaf and sha Other containers containing the aforementioned weeds and crops were treated pre- or post-emergence with the same non-toxic solvent to the plants, thereby controlling the effect of the solvent. A set of untreated plants also served for comparison. Pre-emergence and post-emergence treated plants and plant control samples were maintained in the greenhouse for sixteen days, then all treated plants were compared to their control samples and the effect of the treatment was visually evaluated.

The following rating system was used:

O = no effect = maximum effect C = chlorosis or inecrosis D = dofoliation

E = germination inhibition G = growth retardation H = formative effects U = unusual pigmentation 6Y = fallout of buds or flowers P = disappearance of apex bud B = burns

Compound 1

Compound 6 axes _of ch ₃

Compound 7

OSO, CH

CH _a

OSO ₂ CH _a

/

2. 3

OCH »so _z nh \ _h _ ^

N- (• P ^CH 3

O / * 3

JI N— {

SO, NH 4 N- (O N and N - (ty

Compound 2 och,

Compound 8

OSO ^ CH,

ΛοΎ λ w · <^ SO ^ NH ^ _W _ (0

N

OCH, _ oso.ch »[° Λ» / “·

Compound 9

Ν '

CH _a

OCH,

Compound 3

° 'with NH ^ H- ^(N O:

CH,

Compound 4

OSO ^ CH 3 O

NCH,. Oso, CHCH, fof? _M OCH ₃ ^ ^SO Z ^W

H - ₃

Compound 10

OSO ^ CH ^ CH ^ (° Λ 4 ^! & Ϊ nC ⁴

OCH,

OCH,

Compound 5 oso, ch _{4o ΧΗ3}

2 · n- \

N ~ \

CH _b

Compound 11

OSOpCH ^ CH ^ CHgCHj © / λ Z “ ³ Sat / hr ^z \ _h _ ^ o)

N— \

OCH,

CH,

Compound 12

OSO ^ CH ^ CH ^ CH ^ CH ^

O CH, ' ^Λ ! -N <' SO / JH NW- <O /

N- \

CH,

Compound 13

OSO ^ CH ^ CH ^ CH ^ CH ^

O OCH.

Λ N- (SO.NH NH- (On * H ~ OCH)

Compound 14

OSO / J ^ CWjCWjC / ^

⁰ 1 Λ 4 4 ^CH * so ^ h 'rw ^ Q) _N N— (

CH _Ó

Compound 15 pS0 _of CH _of 0H _of CH 2 CH ₃ ° ¹ Λ 'H'

SOgNH

N ~ \

CL

Compound 16

OSO ^ CH ^ CH ^ CH ^ CH ₃

O CH _Ó

JI js / _ / so HH 4 NH- (C) - - C 1 -N \

Compound 17

OCH,

OSOJCH-,

Qp SO ^ NH NH — ζθ /

OCH,

N- _x

OCH,

CH _Ó

Compound 19

OSO ^ CHj

CH,

O

AND

Cl SO4 NH HH)

CH,

Compound 22

CH

OSO _Z CH _Z

O

AND,

O

H- _(C ^ f ^{<S0.NH /} ^ ^NH - (O / ^C '•' VZ N \ \

H

Compound 24

Compound 29

pso / o)

-o \ Y ^N -1

SONH ^NH ~ (O. i _N.

OCH,

CH,

Compound 30

OSO ^ CH ^

Compound 25

° ^s % ©? Ν-χ so.nh ^ nh -ZO /

CH foT

SO ^ NH ^_ '\

NZ ^nh And och:

OCH,

Compound 26

Compound 31

OSO ^ CH ^

O. ° ¾ eats NZ ⁴

N ~ <

^CW 3

OSO.

CH.

ο 1 II n _- (SOoNW ^ “- << 5 /” ^

Compound 34

Compound 40

OSO ^ CH ^ CH / H ^

Compound 35 ch ₃

NH

Nr (

AOn n /

OCH,

OCH,

OSO ^ CHj

X m ^CHž

SO.NH N ~ (On

CH ^CH S OCH Ή.

Compound 36

OSO ^ CH ^ CH ^ CH ^

O | O. OCH,

Λ NA so ^ nh ^ nhaOnA

OCH,

CH _X * OL w— \

SO.NH (NHAO) ~.

N ~ \

Compound 41

OCH, (O / SO 4 NHCNH-O 2)

Cl OSO CH. OCH ₃

Compound 42? _n 7

O / -SO, NHCNH-

Cl O ^{CH3 SO2}

Compound 43

Cl

OCH,

OCH,

OCH,

Compound 37

OSO ^ CH ^ H / H ^

Λη46>

OCH ^ Ο, Ν & ΝηΪνΗ ^ 0S0 ^ _CH3 CH *

SO ₄ NH

CH *

Compound 38

OSO ^ C ^ CH ^ CH ^

SO 4 NH

O CH,

Λη-αο)

Compound 44

C 1 _{z z} nhcnhAO'n

Target OSO "CH, ~ OCH.

! / (

OCH, n \

CH,

Compound 39 oso CH ^ CH ^ ROT ° CHU J ^{CH ϊ} 'εσ ~ NH' Sw-U-N * N \ ^C%

mp ° C

Compound 50

Compound 45

\ ^ SO ^ CH, ch,

SONH CONH - \ O) N - <CH

Compound 46 '5

216—218

224—227

Compound 51

CH,

NSO, NHCONH- Oy

NOCH

221—224

Compound 52

220—222

Compound 47

228—230

Compound 48

199—200

Compound 53

Compound 49

CH *

212—213

195—197

Compound 54

US0.C1K of so, mhconh- (Qn “N” t

CH, and ₃

218—221

200—201

Compound 55

Compound 56 ch ₃

N- <

SO NNCONN - (O N

Nocn.

OSO _from CN _from CH _from CN _b

O | N ~ / oc / <

SO.NNCONN — ζΟ N N ~ \

OCN,

CN

180-182

151—15

Table A

Rate kg / ha Compound 1 0.1 Compound 2 0.1 Compound 3 0.1 Compound 0.1. Poslemergentně shrimp beans 9C 9C 9C 9C cotton 10C 9C 10 c 9C povijnice 10C 10C 10C 10C beet 10C 10C 9C 10C Oassiia 9C 9C 9C 9C šáchor 9C 9C 9C 1C, 5G rosička 9C 9C 9C 4C, 9G hedgehog, 10C 10C 10 C 4C, 9H deaf oats 2C, 9G 4C, 9G 5C, 9G 0 wheat 1C, 2G 5C, 9G 5C, 9G 0 maize 5C, 9G 9C 9C 4U, 9G soybeans 9C 9C 9C 9C rice 9C 9C 9C 9C clear ok 9C 10C 9C 2C, 9H Preemergence povijnice 9G 9G 9C 9C beet 9H 9H 9H 9H Cassia 9C 5C, 9G 6C, 9G 6C, 9G šáchor 10E 10E 10E 1C, 7G rosička 9C 6C, 9G 2C, 8G 2C, 5G hedgehog 5C, 9H 9C 3C, 9H 7C, 9H deaf oats 1U, 9G 5C, 9H 4C, 9H 8G wheat 5G 5C, 9H 1C, 9H 3G maize 2U, 9G 10E 10E 3C, 9H soybeans 9H 9H 9H 9H rice 10E 10E 10E 10E sorghum 7C, 9H 6C, 9H 10H 1C, 9G

Table A (continued)

Dose kg / h Compound 5 Compound 6 Compound 7

0.1 0.1 0.1

Postemergence

shrimp beans 9C 9C 1C, 2G baivlník 9C 9C 9C povijnice 10C 10C 9C beet 9C 9C 9C Casisia 9C 6C, 9G 5C, 9G šáchor 5G 1C, 5G 2C, 5G rosička 2C, 9G 9C 3G hedgehog 5C, 9H 9C 0 deaf oats 1C, 4G 3C, 9G 0 wheat 0 1C 0 maize 6C, 9G 6C, 9H 3C, 9H soybeans 9C 9C 9C rice 9C 9C 6G sorghum 2C, 9H 6C, 9G 1C, 3G Preemergence povijnice 9C 9C 1C, 3G beet 9H 9H 8H Gassia 6C, 9G 6C, 9G 2C, 2H šáchor 1C, 6G 6G 0 rosička 2C, 6G 1C, 6G 0 hedgehog 2C, 9H 7C, 9H 0 deaf oats 1C, 7G 3C, 9G 0 wheat 0 8G 0 maize 9H 9H 3G soybeans 9H 9H 1C, 2H rice IDE 10E 1C sorghum 5C, 9H 7C, 9H 0 Table A (continued) Dose kg / hia Compound 8 0.05 Compound 9 Compound 10 0.05 0.05 Compound 11 0.05 Postemergence shrimp beans 10G, 9C 9G, 3H, 6C; 7G, 3H, 7C 2C, 2H cotton 10G, 9C 10G, 8C 3C, 2H, 6G sorghum 10G, 4C 10C, 10C, 9C 0 maize 7G, 5H 10G, 8C; 10G, 3H 0 soybeans 10G, 7C 10G, 8C, 7G, 7C 2H, 6G wheat 0 3G, 2C 0 deaf oats 0 9G, 3C, 10G, 6C 0 rice 8G, 3C 10C 10C 1C hedgehog 10G, 6C 10C, 10C, 9C [0100] 2H rosička 0 8G, 3C0 0 povijnice 10G, 9C 7G, 9C, 10G, 5C 9C beet 10G, 9C 10C, 10C, 7C 3C, 9G Gassia 10C 10G, 8C 0 šáchor 10G, 7C 10G, 6C 0 Preemergence sorghum 8G, 5G 9G, 9C 0 maize 6G 9G, 9C, 9C 0 soybeans 8G, 5H 9G, 5H, 8G, 5C 0 wheat 0 7G 7G 0 deaf oats 5G, 3H 8G, 3C, 7G, 5H 0 rice 8G, 6C 8G, 8C 10E 3G hedgehog 8G, 5H 9G, 6C; 8G, 5H 0 povijnice 8G, 5C 8G, 9G 7G beet 8G, 3H 9G, 5C 9G 9P 9G 9P 5H Gassia 9G, 9C, 8G, 9G 0 šáchor 10E 10E 10E 0

Table A (continued)

Rate kg / ha Compound 12 0.05 Compound 13 0.05 Compound 14 0.05 Compound 15 o, i Postemergentoě shrimp beans 1C, 2H 6C, 9G, 6Y 6C, 9G, 6Y 0 baivlník 1C 3C, 3H, 9G 3C, 3H, 9G 0 sorghum 6H 0 0 0 maize 0 0 0 '0 soy-bean ÍH 2H, 6G 2H, 5G 0 wheat 0 0 0 10 deaf oats 0 0 0 0 rice 0 0 0 0 hedgehog 0 0 0 0 rosička 0 0 0 0 povijnice 1C, 5G 4C, 9H 3C, 9H 0 beet 1C 4C, 9H 2C, 8G 0 Cassia 0 3C 1C 0 šáchor 0 0 0 0 Preemergence sorghum 0 0 0 0 maize 0 0 0 0 soy gods 0 0 0 0 wheat 0 0 0 0 deaf oats 0 0 0 0 rice 0 0 0 0 hedgehog 0 0 0 0 rosička 0 0 0 0 povijnice 0 3C, 9G 4C, 9G 0 beet 0 8H, 3C 7H, 3C 0 Cassia 0 2C 0 0 šáchor 0 0 0 0 Table A (continued) Rate kg / ha Compound 16 Compound 17 Compound 18 Compound 19 0.1 0.05 0.05 0.05 Postemergence shrimp beans 0 3C, 5G, 6Y 9C, 7G 6C, 7G, 6Y cotton 0 7C, 6G 8C, 7G 9C, 6G sorghum 0 3C, 4G 2C, 4G 2C, 4G maize 0 4C, 3U, 4G 5C, 6G 0 soy bcib 0 6C, 7G 10C 7C, 6G wheat 0 0 0 2G, 2G deaf oats 0 2C 3C, 4G 3G rice 0 2C, 3G 3C, 4G 3C, 5G hedgehog 0 10C 7C, 6G 2C, 3G rnsička 0 2C, 3G 0 0 povijnice 0 10C 5C, 4G 10C beet 0 10C 8C, 7G 10C Cassia 0 8C, 7G 3C, 4G 3C, 4G šáchor 0 10C 6C, 4G 5C, 4G Preemergence sorghum 0 3C, 6G 5C, 8G 7C, 7G maize 0 3C, 6G 7C, 6G 0 soy-bean 0 7C, 8G 7C, 8G 7C, 6G wheat 0 0 3C, 5G 0 deaf oats 0 2C 7C, 6G 2C, 6G rice 0 10E 8C, 8G 8C, 7G hedgehog 0 7C, 8G 7C, 7G 7C, 5G rosička 0 2C, 2G 3G, 2C 0 povijnice 0 7C, 7G 10C 7C, 6G beet 0 8C, 7G 3C, 5G 5C, 6G Cassia 0 8C, 8G 7C, 6G 5C, 4G šáchor 0 10E 10E 10E

Table A (continued)

Dose kg / hia Compound 20 0.05 Compound 21 0.05 Compound 22 0.1 Compound 30 0.05 Postemergenrtně shrimp beans 2G 9C, 6G, 6Y 3C, 4G, 6Y 3C, 9G, 6Y bavlnlk 5C, 4G 9C, 5G 0 5G, 9G sorghum 4C, 5G 6C, 5G 0 10C maize 10C 7C, 6G 0 10C soy-bean 4C, 5G 5C, 6G 0 2C, 9G wheat 0 2C, 3G 0 9C deaf oats 4G, 5G 8C, 7G 0 2C, 8G rice 3C, 4G 2C, 3G 0 10C hedgehog 7C, 6G 10C 0 10C rosička 2C, 2G 7C, 8G 0 6G, 9G povijnice 10C 10C 0 9C beet 10C 10C 0 9C Cassia 2C 5C, 3G 0 9C šáchor 0 3C, 4G 0 9C Preemergence sorghum 7C, 8G 7C, 8G 0 1C, 9H maize 7C, 8G 8C, 8G 0 1C, 9G soy-bean 6C, 7G 7C, 6G 0 1C, 9G wheat 0 0 0 9G deaf oats 2C, 5G 5C, 6G 0 8G rice IDE 10E 0 10E hedgehog 7C, 7G 8C, 8G 0 5C, 9H rosička 4C, 5G 5C, 7G 0 2C, 8G povijnice 10C 10C 0 9G beet 10C 10C 0 9H Caissia 5G, 6C 7C, 6G 0 2C, 9G šáchor 0 7C, 5G 0 10E Table A {continued] Rate kg / ha Compound 31 0.05 Compound 32 0.05 Compound 33 0.05 Compound 34 0.05 Postomergenitně shrimp beans 9C 9D, 9G, 6Y 9D, 9G, 6Y 4C, 6G, 6Y cotton 8C, 9G 3H, 6C, 9G 6C, 9G 3H, 6C, 9G sorghum 2C, 9G 9C 3C, 9G 1C, 6H maize 7U, 9G IC, 9G 3U, 9G IC ', 5G soy-bean 4C, 9G 5C, 9G 3C, 9G 2C, 9G wheat 2C, 7G 9C 1C, 3G 0 deaf oats 1C, 8G 9C 1C, 2G 0 rice 3C, 9G 9C 2C, 9G 8G hedgehog 9C 10C 10C 3C, 7H rosička 6G 2G, 5G 1C, 3G IC, 3G povijnice 10C 10C 3C, 9G 9C beet 10C 9C 6C, 9G 6C, 9G Gaissia 9C 9C 3C, 7G 3C, 5G šáchor 1C, 9G 4C, 9G 2C, 7G IC, 3G Preemergence sorghum 4C, 9G 3C, 9H 2C, 9G 2C, 7G maize 2C, 9G 2C, 9H 1C, 9G IC, 8G soy-bean 8H 3C, 7H 9H IC, 9H wheat 9G 3C 0 0 deaf ov-ea 2C, 9H 1C, 9G 1C, 5G 0 rice 2C, 9H 10E 9H 2C, 5G hedgehog. 2C, 9H 2C, 9H 3C, 8H IC, 5H rosička 2C, 9G 1C, 3G 1C, 3G 0 povijnice 9C 9G 1C, 9H 2G, 9G beet 9H 9H 9H 9H Cassia 2C, 9G 2C, 9G 9G, 3C 6C, 9G šáchor 1OE 10E 1C, 9G 3G

Table A (continued)

Dose kg / h <a Compound 35 0.1 Compound 38 0.05 Compound 37 0.05 Compound 38 0.05 Postemergence shrimp beans 2G 5C, 9G, 6Y 9C 4C, 9G, 6Y cotton 3C, 3H, 7G 9C 9C 5C, 9G sorghum 1C, 3G 9C 3U 10C maize 0 1C, 2G 2C 2C, 4G soy-bean 2C, 9G 2C, 8G 2C 1H, 6G wheat 0 0 0 0 deaf oats 0 2G 1C 5G rice 0 4C, 9G 2'C 7G hedgehog 0 3C, 9H 10C 3C, 7H rosička 0 2C, 4G 3C 2C, 5G povijnice 6C, 9G 9C 9C 2C, 9G beet 4C, 9G 10C 10C 9C Oaissia 2C 5C, 9G 5G šáchor 1C, 2G 9G 1C 8G Preemergence sorghum 0 2C, 9H 2C, 9H 2C, 9H maize 0 2C, 5G 2C, 8H 2C, 7H soy-bean 0 1C, 4H 2C, 5G 2G wheat 0 0 3G 0 deaf oats 0 1C, 6G 1C, 8G 1C, 6G rice 0 3C, 9H 2C, 8H 2C, 6G hedgehog 0 2C, 8H 2C, 9H 3C, 5G rosička 0 1C 1C, 3G 1C povijnice 0 9G 9G 1C, 6G beet 0 9H 9H 9H Cassia 0 2C, 8G 2C, 8H 1C šáchor 0 9G 9G 5G Table A (continued) Dose kg / hia Compound 39 Compound 40 Compound 23 Compound 24 0.05 0.4 0.05 0.05 Postemergence shrimp beans 9C 0 3G 1H cotton 9C 1C 0 0 sorghum 1C 4G 0 2G maize 1C 0 0 3G soy-bean 1H 0 7G 1H wheat 0 0 0 0 deaf oats 2G 0 0 0 rice 0 2G 0 4G hedgehog 2G 0 0 0 rosička 1C 5G 0 3G povijnice 9C 3G 0 2G beet 10C 3G 2G 1C Gassiia 0 šáchor 2G 3G 0 0 Preemergence čirok 1C, 7G 0 0 4H maize 1C, 3G 0 0 0 soy-bean 1C 1H 1H 1C, 1H wheat 0 0 0 0 deaf oats 0 0 0 0 rice 2C 0 0 2C hedgehog 1C, 4H 0 0 0 rosička 1C 2G 0 1C povijnice 9G 3G 0 0 beet 9H 5H 0 2C Cassia 2C, 9H 0 0 0 šáchor 2G 0 0 3G

Table A (continued)

22G433

Dosage kg / bia Compound 25 Compound 28 Compound 27 Compound 28 0.05 0.05 0.05 0.4 Postemergenitině shrimp beans 0 3C, 9G, 6Y. 1C, 2G, 6Y 0 cotton 0 2C 1C 0 sorghum 0 0 3G 0 maize 0 2C, 3G 1C 0 soy-bean 0 [0100] 2H [0100] 2H 0 wheat 0 0 0 0 deaf oats 0 0 0 0 rice 0 0 4G 0 hedgehog 0 0 0 0 rosička 0 0 1C 0 povijnice 0 2C, 6H 1C 3B beet 0 2C, 6G 3C, 6H 0 Gassia 0 Šáchor 0 0 1C 0 Preemergence sorghum 0 0 0 0 maize 0 0 0 0 soy-bean 0 0 0 0 wheat 0 0 0 0 deaf oats 0 0 0 0 rice 0 0 0 0 hedgehog 0 0 0 0 rosička 0 0 0 0 povijnice 0 0 0 0 beet 0 0 9H 0 Cassia 0 0 0 0 šáchor 0 0 0 0 Table A (continuedJ Dose kg / lna Compound 29 Compound 41 Compound 42 0.05 0.4 0.4 Positemergentně shrimp beans 0 9C 9C cotton 0 10C 4C, 3H, 9G sorghum 0 6U, 9G 2C, 9G maize 0 2U, 9H 5U, 9G soy-bean 0 9C 9G wheat 0 2G 0 deaf oats 0 1C, 8G 0 rice 0 6C, 9G 6C, 9G hedgehog 0 5C, 9H 1C, 8G rosička 0 2C, 6G 4G povijnice 1C, 2G 6C, 9G 6C, 9G beet 0 10C 9C Cassia 9C 4C, 7H šáchor 0 2C, 8G 2C, 5G Preemergence sorghum 0 5C, 9H 5C, 9G maize 0 2U, 9G 2C, 9G soy-bean 0 9H 4C, 8H wheat 0 8G 2C, 8G deaf oats 0 4C, 8G 2C, 8G rice 0 10E 10E hedgehog 0 4C, 9H 4C, 9G rosička 0 5G 1C, 4G povijnice 0 9C 9C beet 0 9H 9H Caslsia 0 4G, 9G 3C, 7G šáchor 0 1C, 9G 8G

Table A (continued)

Compound 43 Compound 44

Dose kg / ha 2 6 2 6 Postemergenitně shrimp beans 0 3C 0 0 cotton 0 3C 0 2C sorghum 0 0 0 2C maize 0 0 0 0 soy-bean 0 1C 0 3G wheat 0 0 0 0 deaf oats 0 0 0 0 rice 0 0 0 0 hedgehog 0 1C 0 0 rosička 0 0 0 0 povijnice 0 0 0 1C, 3G beet 0 0 0 0 Caissia 0 1C 0 0 šáchor 0 0 0 0 Preemergence sorghum 0 1C, 5G 0 2C maize 0 2C, 5G 0 1C, 2G soy-bean 0 0 0 0 wheat 0 0 0 0 deaf oats 0 1C, 4G 0 0 rice 0 1C 0 1C hedgehog 0 5C, 8H 0 5C rosička 0 2G 0 0 povijnice 0 3C 0 2C beet 0 2C, 8H 0 5H GaSsia 0 3G 0 5G šáchor 0 0 0 0 Table A (continued) Rate kg / ha Compound 45 Compound 46 Compound 47 Compound 48 0.05 0.05 0.05 0.05

Postemergenitně shrimp beans 4C, 9G, 6Y 9C 9C 4C, 8G, 6Y cotton 6C, 9G 6C, 9G 8C, 9G 3C sorghum 2C, 9G 5C, 9G 8U, 9G 2C, 9H maize 3G 3C, 9H 5U, 9G 3C, 9H soya 1C, 8H 5C, 9G 9C 2C, 6G, 5X wheat 1C 1C 1C 0 oat deaf 2C, 8G 3C, 9G 2C, 9G 2C, 7G rice 3C, 9G 5C, 9G 5C, 9G 2C, 8G, 5X hedgehog 5C, 9H 9C 6G, 9H 2C, 8H rosička 3C, 7H 4C, 9H 9C 0 povijnice 6C, 9G 9C 7C, 9G 3C, 8H beet 5C, 9G 9C 9C 1C, 4G Gaislsia 3C, 6H 5C, 9H 5C, 9G 1C, 3G šáchor 5C, 9G 10C 9C 3G Preemergence sorghum 3C, 9H 10H 3C, 9H 1C maize 2C, 8G 9G 9G 1C, 3G soya 2C, 2H 9H 9H 1H wheat 0 5G 0 0 oat deaf 3C, 8H 3C, 9H 9H 3G rice 4C, 8H 5C, 9H 10 E 1C hedgehog 3C, 7H 6C, 9H 4C, 9H 2C rosička 1C, 5G 3C, 8H 2C, 8G 0 povijnice 3C, 9H 2C, 9H 2H, 9G 1C beet 2C, 8H 9H 9H 0 Cassia 5C 3C, 9G 5C, 9G 1C šáchor 10E 10E 10E 0

Table A (continued)

Dosage kg / hia Compound 49 0.05 Compound 50 0.05 Compound 5.1 0.05 Compound 52 0.05 Positemergentně shrimp beans 9C 9C 0 3C, 3H, 6Y cotton 6C, 9G 6C, 9G 0 2C, 2Ή sorghum 9C 9C 0 2C, 4G maize 9C 7U, 9C 0 1C, 5H soya 9C 4C, 9G 0 2C, 6H wheat 2U, 9G 2C 0 0 oat deaf 3C; 9G 2C, 4G 0 0 rice 6C, 9G 5C, 9G 0 4G hedgehog 9C 5C, 8H 0 2C, 4H rosička 9C 3C, 9G 0 0 povijniee 4C, 9H 4C _f 9H 0 3C, 7H beet 4C, 9H 4C · 9G 0 3C, 9G Cassia 5C, 7H 4C, 6H 0 3C šáchor 2C, 4G 3G, 5X 0 8G Preemergentaiě sorghum 10H 5C, 9H 0 2C, 6G maize 3C, 9G 2C, 9G 0 3C, 7G soya 3C, 5H 2C, 5H 0 1C wheat 1C 2C 0 0 oat deaf 3C, 9G 2C, 5G 0 0 rice 9H 9H 0 1C, 3G hedgehog 3C, 9H 3C, 9H 0 2C, 8H rosička 1C 1C 0 1C povijniee 4Ci 9H 2C, 9G 0 6H, 2C beet - 9H 0 3C, 8H Cassia 3C, 3H 2C, 3H 0 1C šáchor 1C 3G 0 1C, 8G Table A (continued) Dosage kg / ba Compound 53 0.05 Compound 54 0.05 Compound 55 0.05 Compound 56 0.05 Positemergemtně shrimp beans 4C, 9G, 6Y 1C 3C, 9G, 9C cotton 4C, 7H 1C, 2G 2C, 6G 6C, 9G sorghum 1C, 3G 0 2C, 9H 2G maize 1C 0 3U, 9G 0 soya 2C, 8H 1H 3C, 9G 2C, 8H wheat 0 0 0 0 oat deaf 0 0 0 0 rice 4G 0 1C, 6G 0 hedgehog [0100] 2H 0 4H 0 rosička 0 0 0 0 povijniee 3C, 8G 2C, 7H 3C, 9G 6C, 9G beet 4C, 9G 4G 3C, 9H 9C Cassia 1C, 3G 1C 0 5C, 8G šáchor Preemergence 1C, 8G 0 0 0 sorghum 1C, 4G 0 1C, 4G 4G maize 1C, 4G 1C, 5G 3C, 7G 0 soya 1C 1H 1C 0 wheat 0 0 0 0 oat deaf 0 0 0 0 rice 1C, 4G 2G 1C, 3G 2G ježatka 3C 2C 1C 2C rosička 1C 0 0 0 povijniee 8G, 2C 0 8H, 2C 9C beet - 0 - 9H Calssia 0 0 0 5C, 9G šáchor 9G 0 0 5G

22P433

and. mp 183-186 ° C

Dose (kg / ha 0.04 Postemergence potato bean 9C cotton 9C sorghum 10C maize 5U, 9C soya 9C wheat 2C, 9G oat deaf 3C, 9G rice 9C hedgehog 9C rosička 5C, 9G povijnice 9C beet 10C Cassi a 9C šáchor 10C diabetes - Preemergence sorghum 4C, 9H maize 6C, 9G soya 9H wheat 3C, 9G oat deaf 3C, 9G rice 10E hedgehog 7C, 9H rosička 3C, 9H povijnice 2C, 9G beet 9H Cassia 5C, 9G šáchor 10E diabetes -

Test B

Two plastic troughs were filled with fertilized and lime Falsington clay soil. One trough was planted with corn, sorghum, meadow-grass and several grassy weeds. The second trough was planted with cotton, soybeans, flatwood, oval (Cyperus roitundusj and several broadleaf weeds) and the following grassland and broadleaf weed species were planted: Rosette (Digitaria sainquinelisj, hedgehog (Echinochloa crusgallies), Deaf-grass) Sorghum halepense), Paspalum dilatatum, Foxtail (Seitaria. Faberii), Corn Brome (Bromus secalinus), Mustard (Brassica arvenslsj), Beetle (Xanthium pensylvanicum), Hairy Pigweed (Amaranthus retroflexus), Ipomoea Cassederacea (Cassia hederacea) , weed of tea plantations (Sida spinosa), Abutilon (Abutilon theophrasti) and Durman (Datura stramoniumj). In addition, rice and wheat seeds were planted with a 12.5 cm plastic container filled with the same prepared soil. 5 cm of the sugar beet was sown and all four of the above containers were pre-emergence treated with n several test compounds of the invention.

Twenty-eight days after treatment, a visual evaluation of the effect of the chemical treatment was performed using the evaluation system described above for Test A. The results are summarized in Table B.

and

Table Β

Preemergence treatment on Fallsington clay soil

Dose kg / ha Compound 1 Compound 2

0.03 0.12 0.03 0.12 rosička 7G, 2H 8G, 3H 7G, 3H 8G, 3H hedgehog 8G, 3H 9G, 9C 9G, 8C 1OC sorghum 9G, 9C 10C 10C 10E Deaf oats 6G 10C 8G, 5C 9G, 9C Sorghum 8G, 7C 10C 9G, 9C 10C Paspalum dilatatum 7G 9G, 9C 8G, 3H 8G, 3H Sejtaria faiberii 6G, 3C 8G, 5C 5G, 3C 10C lipniee. meadow 8G, 9C 10C 8G, 9C 10C corn brome 8G, 9C 9G, 9C 10E 10E sugar beet 10C 10G 10C 10C maize 5G, 3U 8G, 5H 7G, 5H 10C mustard 10C 10C 10C 10C beet 6G - 5G 10C Woolly Pigweed 10C IDE 7G 10E šáchor 10E 10E 6G 10E havlník 8G 9G, 5G 6G, 3H 9G, 8C povijnice 5G 9G, 9C 7G 9G, 5C Caissia 8G, 8C 10C 7G, 4C 9G, 9C Siná sípimosa 6G 9G, 8C 6G, 3H 8G, 6C Abutilon theoiphrasti 9G, 8C 10C 8G, 8C 9G, 9C durman obecný 7G, 3C 9G, 8C 9G, 9C 9G, 9C soy gods 8G, 5H 9G, 8C 7G, 5H 9G, 8C rice 8G, 3H 10E 8G, 7C 10E wheat 0 3G 5G 8G, 9C Table B (continued Preemergence treatment for Fallsington clay soil Rate kg / ha Compound 3 0.007 0.015 0.03 0.12 rosička 0 0 5G 8G hedgehog 2G 2G 8G, 3H 9G, 9C sorghum 2G 4G 10C 10E deaf oats 0 0 10C 10C Sorghum 0 3G 10C 10C Paspalum dilatatum 0 3G 6G 8G, 3H Seítariu faberii 0 3G 3C 7G, 3C Limegrass 0 2G 10C 8G, 8C corn brome 0 - 10E 10E sugar beet - 4G 10C 10C maize 0 0 4 10C 10C mustard 5G 7G, 3C 10C 10C beet 0 0 7G 8G, 5H Weasel Weasel 0 10E 9G, 9C 10C šáchor 0 0 10E 10E cotton 0 0 8G, 3C 9G, 7C povijnice 3G 3G 8G 9G, 7C Cassia 0 0 9G, 8C 9G, 8C Siná spinosa - 0 4G 10C Abutilon theophrasti 0 0 8G, 5E 9G, 8C durman obecný 0 0 8G, 8C 9G, 9C soy gods 0 0 8G, 5H 9G, 8C rice 3G 6G, 3H 10E 10E wheat 0 0 5G 7G, 3C

Table Β (continued J

Preemergence treatment at Fallsington is hunting her land

Dose kg / ha Compound 36 Compound 39

0.06

rosička 2G hedgehog 4G sorghum 6G, 3H deaf oats 4G Sorghum 4G, 3H Paspalum dilatatum 4G Sětaria faberii 4G lipnice- luční 6G corn brome 6G sugar beet 6G, 6C maize 3G mustard 10E beet - Woolly Pigweed 5G, 5C šáchor 7G cotton 4G povijnice 4G Cassla 6G Siná spinosa 5G, 3C Abutilon theophrasti 5G, 3H durman obecný 3G soy gods 2G rice 3G wheat 0 Test C

The high herbicidal activity of the two compounds within the scope of the invention is apparent from the results obtained in this experiment. The experiment dealt with pre-emergence application to soil. The plastic containers used were 25 cm in diameter and were filled with Fallsington clay soil. One group of pots was planted with weeds whose seeds were homogeneously mixed with the top soil to a depth of 1.2 cm. The following weed species have been selected: Sorghum halepeinise j, Echinochloa crusgQlliJ, Digitaria sanguinalisj, Setaria faberii, Abutilon theophrasti, Datura stramonium, Mustard (Brassica arvhus) and Lask. a group of pots were planted with the following crops in an amount of one to four species

0.25 0.06 0.25

4G 2G 2G 6G, 5H 4G 5G 8G, 5H 4G 4G, 2H 4G 3G 3G 6G, 3H 4G 3G 5G 3G 0 6G, 3H 0 2G 7G 2G 4G 7G 0 3G 8G, 9C 9G, 8C 10C 4G 2G 4G 10E 8G, 8C 8G, 9C 8G, 7C 8G, 5H 10C 9G, 9C 4G 6G, 4C 10E 4G 6G 8G, 3H 8G, 3H 9G, 5C 8G, 9C 9G 9G, 3C 8G, 8C 5G, 3C 7G, 8C 6G, 3C 6G, 2C 6G, 3C 8G, 8C 7G, 3H 8G, 9C 5G, 5C 7G, 3C 8G, 5C 5G, 3H 3G 4G 5G 0 0 0 0 0

in one container: corn (sowing depth 3.7 cm), cotton, soy gods, sunflowers, oats (Clinton oatsj, wheat, beans (Black Valentine beáne), rice, sorghum, peas, flax, peanuts (all up to 2, 5 cm), cucumbers, sauerkraut, alfalfa, safflower, sugar beet, tomatoes, spinach, barley and meadow meadow (all to a depth of 1.2 cm).

Immediately after sowing, the test chemical was applied to the soil surface after dissolution in a non-toxic plant solvent. One pot from the weed group and one from each crop group were left untreated as a control. The treated and untreated plants were immediately irrigated with approximately 4 mm artificial irrigation and then left in the greenhouse for several weeks. Visual evaluation of the effects on weeds and crops was performed 28 days after treatment using the evaluation system described above for Test A. Data are shown in Table C.

Table C

Preemergeinite treatment on Fallsington clay soil

Rate kg / ha Compound 1 0.0035 0.0075 0.0150 0.03 maize 5G, 3C cotton 7G, 3H soybeans 4G, 2H peanuts 6G sunflower 5G oat 4G wheat 2G sorghum 7G, 5H sugar beet 9G, 9C pea IDE only 6G lucerne 8G, 6C bean 0 spinach 8G, 5H cabbage 8G, 6C tomatoes 4G rice 6G flare 7G, 4C cucumbers 5G meadow meadowgrass 7G barley 3G broadleaf weeds 3G 4G 6G, 2H - grass 0 0 2G - Table C (continued) Preemergeinite treatment for Fallsington clay soil Rate kg / ha Compound 2 0.0075 0.015 0.030 0.06 maize 9G, 9C cotton 10E soybeans 9G, 5H peanuts 8G, 3H sunflower 9G, 5H oat 6G, 2C wheat 5G sorghum 10E sugar beet 10E pea 10E only 10E lucerne 8G, 6C bean 8G, 5H spinach 9G, 9C cabbage 8G, 7C tomatoes 5C, 8G rice 10E flare 8G, 7C cucumbers 9G, 5Ή meadow meadowgrass 6G, 5H barley 8G, 7C broadleaf weeds 5G, 3C 7G, 5C 9G, 8C grass 6G, 3C 8G, 4C 9G, 6C -

Test D

Two 25.4 cm (1 inch) plastic containers with polyethylene foils were filled with prepared Fallsington clay soil. One pot was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), deaf oats (Avena fatua), roof brome (Bromus tectorum), corn brome (Bromus secalinus), black fox (Alopecurus myosuroides), lipnice ), green grass (Setaria viridie), creeping grass (Agropyron repens), ryegrass (Lolium multiflorum) and Bromus rigidus.

The second pot was planted with seeds of potassium salmon (Salsola káli), eel (Descuraina pinnata), cotton (Polygonum pensylvanicum), topmost Sisymbrium altissium, kochia (Kochia scoparia), capsule paste (Caipsella inodora), , black eggplant (Solanum nigrum), barborka villageTable D

Rate kg / ha

0.002e (Barbarea vulgaris), mustard (Brassica kabei ·) and bindweed (Polygonum convolvulus). The above two containers were pre-emerge treated. At the same time, the above plants were treated post-emergence in two additional containers. The height of these plants at the time of treatment ranged from 1 to 15 cm depending on the plant species.

The applied compounds were diluted with a non-toxic plant solvent and sprayed onto the soil surface. For comparison, untreated and solvent-treated plants were included in the experiment. The treated plants were kept in the greenhouse for 20 days, when the effect of the treatment was compared with the control samples by visual evaluation. The results in Table D show that certain compounds of the invention are useful for pre-emergence and / or post-emergence weed control in cereals such as wheat and barley.

Compound 1

0.008 0.008 0.015

Preemergence 0 wheat barley 0 deaf oats 0 roof brome 3G corn brome 5G psárka 3G lipnice 5G bér 0 pýr 3G rye grass 0 Bromus rigidus 2G salmon 0 eel 6G rdesno - hulevník 3C, 8G Kochia 1G kokoška 3C, 5G Matricaria inodora 4G eggplant 2C, 4G barborka 2C, 7G mustard 5C, 6G wafer 3G

0 0 0 0 0 1C, 6G 0 0 3C, 7G 2C, 5G 1G 5C, 7G 4C, 7G 3G 10C 5C, 6G 2G 10C 2C, 6G 1C, 2G 7C, 8G 2G 3C, 4G 3C, 5G 3C, 5G 0 8G 3C, 5G 0 4G 2C, 4G 0 2C, 5G 0 1G 8C, 7G 8C, 8G 8C, 8G 10C 10C 7C, 7G 10C 5G 3G 9C, 8G 8C, 8G 9C, 8G 10C 7C, 8G 7C, 7G 10C 4C, 6G 6C, 7G 8G 4C, 8G 7C, 7G 10C 8C, 8G 7C, 7G 10C 2C, 4G 1C, 2G 3C, 6G

Table D (continued)

Rate kg / ha

Compound 1

0.002 0.008 0.008 0.015

Postemergence wheat 0 0 0 0 barley 0 0 0 3C, 5G deaf oats 0 1C 0 3 (2G brome 3G 5C, 7G 4C, 5G 3G corn brome 4C, 7G 8C, 7G 8C, 7G 1OC psárka 6G 4C, 5G 7C, 7G 1OC lipnice> 3G 3C, 6G 3C, 5G 5C, 4G bér 4G 7C, 7G 7C, 7G 3C, 4G pýr 3G 6G 2C, 3G 6C, 5G eats lek 2G 2G 0 3G Bromus rigidus 2G 5G 0 2G salinobýl 2C, 3G 10C 9C, 7G 10C eel 10C 10C 1OC 10C rdeisno _ hulevník 4C, 6G 10C 10C 10C Kolchia 3G 4G 10G 8C, 7G kokoška 10C 10 C 10C 1OC Matricaria inodora 7C, 7G 10C 9C, 7G 10C eggplant 4G 4C, 6G 1C, 1G 0 barborka 3G 10C 10C 10C mustard 1OC 10C 10C 10C opletka 2C, 4G 5C, 5G 6C, 5G 10C Table D (continued) Rate kg / ha Compound 1 0.03 0.06 0.03 0.06

Postemergence wheat barley deaf oat brome with | cherry brome cereal fox-tail lipnico barley ryegrass

Bromus rigidus salmon eel

Kcxchla kokoška

Matricaria inodora aubergine barborka mustard wafer

1C, 1G 0

2C, 7G 5C, 7G 5C, 7G 7C, 7G 2C, 3G 1C, 3G

2C, 3G

10C

10C

7C, 8G

10C

7C, 7G 8C, 7G 8C, 9G 8C, 8G 3C, 4G

2C, 3G 6C, 8G 8C, 8G 10C 10C 10C 10C 9C, 8G 10C 4C, 7G 5C

10C 10C 10C 10C 3C 8C 10C 10C 4C 8C

2C, 2G, 2G

7C, 7G

10C 10C 6C, 7G 7C, 8G 3C, 6G2C, 4G2C, 3G 10C 10C

10C 10C 10C 9C 8G 3C 7G 10C 10G 7G 6G

1C, 2G 7C, 6G 3C, 3G 3C, 4G 10C 10C 10C 7C, 6G 7C, 6G 4C, 5G 3C

10C 10C 10C 10C 4C, 5G 10C 10C

Table D (continued) Dose kg / ha

Compound 2

0.002 0.008 0.008 0.015

Preemengenitae wheat barley deaf oats bark rooftop bean corn foxgrass lindengrass

Bromns rigidus salmon eel

Kochia kokoška

Maitricaria Inodora aubergine barborka mustard braid

Table D [continued] Dose kg / ha

0 0 0 2C, 2G 0 3G 3C, 4G 5C, 7G 0 2C, 5G 2G 8C, 8G 6G 7C, 7G 3C, 7G 10C 5C, 7G 10C 5C, 8G 10C 3C, 6G 7C, 7G 3C, 7G 10C 1C, 6G 7C, 7G 2C, 5G 10C 0 4C, 5G 2C, 4G 6C, 7G 4G 3C, 6G 4G 8C, 9G 3G 5C, 7G 5C, 7G 9C, 9G 5G 6G 3C, 4G 9C, 9G 0 1C, 1G 3C, 4G 9C, 9G 3C, 8G 8C, 9G 7C, 8G 10C 7C, 8G 10C 10C 10C 2G 5G 7C, 8G 8C, 9G 8C, 8G 8C, 8G 10C 10C 5C, 8G 7C, 8G 7C, 7G 10C 3C, 4G 3C, 4G 5C, 6G 2C, 7G 8G 2C, 9G 7C, 7G 1OC 7C, 8G 8C, 8G 7C, 8G 1OC 2C, 1G 3C, 4G 3C, 2G 3C, 4G

Post-Temergence Wheat Barley Deaf Oats Bean Cherry Bean Cereal Feathergrass Limegrass

Rye rye

Bromus rigidus salmon eel

Kochia kokoška

Matricaria inodora aubergine barborka mustard braid

Compound 2 0,002 0.008 0.008 0.015 0 1G 1G 5C, 5G 0 3G 2C, 3G 7C, 6G 0 2C, 5G 5G 7C, 7G 3C, 5G 7C, 7G 7C, 7G 7C, 7G 6C, 7G 10C 1OC 10C 2C, 6G 7C, 7G 7C, 7G 10C 5C, 6G 10C 6C, 5G 10C 3C, 5G 4C, 5G 7C, 8G 6C, 6G 1C, 6G 4C, 6G 6G 7C, 6G 1C, 5G 3C, 6G 3C, 6G 10C 4G 1C, 7G 3G 4C, 6G 5C, 4G 8C, 7G 10C 10C 10C 10C 10C 10C 7C, 8G 8C, 8G 10C 10C 5G 10C 10C 7C, 6G 10C 10C 10C 10C 10C 10C 7C, 7G 10C 2G 3C, 5G 1C, 1G 0 10C 10C 8C, 8G 10C 10C 10C 10C 10C 2C, 2G 3C, 5G 6C, 6G 10C

Table D (continued) Dose kg / hia

Compound 2

Preemergence Positemergenitně

0.03 0.06 0.03 0.06 wheat 2G, 4G 4C, 6G 1C, 2G 7C, 7G barley 6C, 7G 8C, 8G 4C, 6G 10C deaf oats 7C, 6G 9C, 8G 5C, 6G 8C, 7G brome 7C, 8G 10C 8C, 7G 10C corn brome 10C 10C 10C 10C psárka 8C, 7G 10C 10C 10C lipnice 5C, 6G 10C 10C 10C bér 4C, 6G 9C, 9G 8C, 8G 7C, 7G pýr 7C, 7G 9C, 9G 4C, 6G 10C eats lek 7C, 8G 10C 5C, 7G 10C Bromus rigidus 6C, 7G 9C, 9G 4C, 4G 9C, 8G slalnobýl 5C, 6G 10C 10C 10C eel 9C, 9G 10C 10C 10C rdesno - - - hulevník 10C 10C 10C 10C Koichila 9C, 8G 9C, 9G 10C 10C kokoška 10 C 10C 10C 10C Maitricaria imodora 7C, 8G 10C 8C, 7G 10C eggplant 7C, 6G 5C, 8G 3C, 4G 2G barborka 10C 10C 10C 10C mustard 9C, 8G 10C 10C 10C opletka 4C, 5G 5C, 6G 7C, 8G 10C

Table D (continued)

Compound 3

Preemergent Postemergeimtně

Dose kg / hia 0.008 0.03 0.008 0.03 wheat 0 1C, 2G 0 1C, 2G barley 2G 7C, 6G 0 4C, 6G deaf oats 1G 7C, 7G 0 7C, 5G brome 4G 10G 6C, 7G 7G, 7G corn brome 2C, 5G 10C 7C, 7G 10C psárka 7C, 7G 10C 4C, 5G 10C lipnice 3C, 4G 5C, 6G 4C, 6G 5C, 7G bér 2C, 3G 5C, 4G 2C, 4G 6C, 7G pýr 0 3C, 4G 2C, 3G 4C, 6G rye grass 3G 7C, 7G 3C, 6G 5C, 6G Bromus rigidus 0 10C 1C, 2G 3C, 4G slalnobýl 0 7C, 7G 3C, 2G 10C eel 4C, 5G 9C, 9G 8C, 7G 10C rdesino - - - hulevník 7G 10C 10C 10C Kochiia 6G 10C 4G 10C kokoška 7C, 7G 10C 9C, 8G 10C Mattricarla inodora 6C, 7G 7C, 7G 6C, 5G 9C, 8G eggplant 3C, 4G 5C, 6G 4G 8C, 8G barborka 7G 7C, 7G 2C, 5G 10C mustard 5C, 7G 7C, 8G 10C 10C opletka 0 2C, 3G 2C, 2G 5C, 6G

Table D (continued)

Rate kg / ha Compound 36 Preemergence Postemergence 0.015 0.06 0.015 0.06 wheat 0 0 0 0 barley 0 0 0 0 deaf oats 0 0 0 0 roof brome 3G 6G 0 3G corn brome 7G 10C 1G 3C, 5G psárka 6G 3C, 7G 2G 5C, 4G lipnico 6G 7C, 7G 2G 3G bér 2G 3C, 5G 1G 2G pýr 0 2G 0 0 rye grass 1G 3G 0 0 Bromus rigidus 2G 2C, 7G 0 2G salmon 0 1G 0 2G rdesno - - - - eel 2G 2C, 5G 5C, 4G 7C, 8G hulevník 5G 3C, 7G 10C 10C Kochia 0 5C, 6G 0 0 kokoška 7G 3C, 8G 7C, 8G 10C Maitricaria iinodora 3C, 8G 7C, 8G 7C, 7G 9C, 8G eggplant 4G 1C, 5G 2G 4C, 5G barborka 3C, 8G 10C 7G, 7G 10C mustard 7C, 8G 10C 10C 10C opletka 3G 1C, 4G 1C, 2G 5C, 4G Tesit E inset seedlings. Test yourself performed in green- and evaluation effects treatment was The test samples were after adjustment added kept at marked intervals after application. directly to the irrigation water rose three days after kaci. Detected data: Compound 1 Dose g / ha Rice 4 days Rice · 4 weeks Hedgehog * 4 weeks Anchor ** 4 weeks

1 0 0 0 7G 4 0 0 0 8G 8 0 0 0 9G Compound 36

• Dose g / ha Rice 1 week Rice 8 weeks Ježatka * 8 weeks Kotvice * * 8 weeks Šípatka *** 8 weeks 25 0 0 0 10C 0 * 100 ALIGN! 0 0 0 10C 0

Echinochloa spp.

Eleocharis spp.

*** Sagittaria spp.

The results show that the compounds of the invention can be used to selectively control weeds in rice cultivation.

Test F

Test substances dissolved in a non-toxic plant solvent were applied by complete spraying of leaf parts and surrounding soil of selected plant species. One day after treatment, observations were made for possible rapid burns to the plants. Approximately fourteen days after treatment, a visual comparison of the treated plants and the untreated control plants was performed and the effect of the treatment evaluated. The rating system was the same as above for Test A. Data are shown in Table F.

All plants were planted in Woodstown sandy-loam soil and grown in a greenhouse. The following plant species were grown in soil in plastic containers (25 cm in diameter and 13 centimeters deep): soy gods, almonds, alfalfa, corn, rice, wheat, sorghum, Abutilon theophrasiti, Sesbania exaltata, Cassia (Cassia tora) ), Beetle (Ipomoea hederacea), Common Durman (Datura sitramonium), Beetroot (Xanthium pensylvanicum), European Tree Dew (Digitaria ssp.), Flatsedge (Cyperus rotudus), Hedgehog (Echinochloa crusgalli), Deer (Setaria faberii), and Deaf (Avena fatua). The following plant species were grown in soil placed in paper containers (12 cm diameter and 13 cm depth). All plants were sprayed approximately 14 days after planting.

Some of the compounds tested in this manner are suitable for post-emergence weed control in wheat cultivation. Compound 39 is useful for post-emergence weed control in soybean cultivation.

Table F

Treatment of leaf part and soil surface

Dose kg / ba 0.06 soybeans 10G, 7C Abutilon ftheophrasti 10G, 7C Sesbania 9C Cassia 10G, 7C cotton 10G, 7C povijnice 10G, 5C lucerne 9C durman 9C beet 10G, 7C maize 10C rosička 8G, 4C rice 8G, 3C šáchor 10C hedgehog 10C wheat 0 bér 10G, 3C deaf oats 6G sorghum 10C mustard - sunflower - sugar beet -

Compound 1

0.015 0.007 0.003

10G, 7C 9G, 5C 9G, 5C 8G, 3C 9G, 9C 10G, 9C 9C 10C 10C 8G, 2C 9G, 5C 10G, 5C 7G, 3C 10G, 9C 10C 9G, 4C 10G, 8C 10G, 8C 5C 6G, 2C 6G, 2C 7G, 3C 0 0 9G, 3C 7G 5G 9G, 7C 8G, 2H 9G, 1 H 2C 5G 0 3G, 1C 8G, 5C 7G, 2C 10C 5G 3G 10C 9G, 4C 9G, 2C 0 0 1G 7G, 3C 5G 5G 3G 3G 3G 9C 8G, 3C 7G, 4U - 10C 10C - 10C 10C - 10C 9G, 9C

Table F (continued)

Treatment of leaf part and soil surface

Compound 2

Rate kg / ha 0.06 0.015 soybeans 9C 10G, 8C Abutilon theoprasti 10G, 4C 5G Sesbania 10C 9C Cassiía 10G, 7C 7G, 3C cotton 10G, 6C 7G, 3C povijnice 10C 8G, 2C lucerne 10C 7C durmlan 10C - beet 10G, 8C 10G, 7C maize 10C 10G, 7U rosička 10C 6G, 1C rice 10C 6G, 3C šáchor 10C 2C hedgehog 10C 6G, 3C wheat 9C 1C bér 10C - deaf oats 10C 5C, 3C sorghum 10C 8G, 5C mustard _ sunflower __ -, sugar beet - - '

Table F (continued)

Treatment of leaf part and soil surface

Dose kg / ha Compound 3

0.06 0.015 0.007 0.003

soybeans 10G, 6C 10G, 4C 9G, 7C 10G, 5C Abutilon 7G, 2C 5G 8G, 8C 7G Sesbanla 9C 9C 8G, 5C 9G, 8C Cassia 10G, 7C 5G, 3C 10G, 5C 8G, 4C cotton 10G, 6C 10G, 6C 10C 8G, 2C povijnice 9G, 4C 9G, 3C 10G, 8C 7G, 1H lucerne 9C 8C 7G 6G, 2C durman 9G, 3C - - 0 beet 10G, 7C 10G, 7C 4G, 5C 3G maize 10C 9G, 6C 9G 9G, 1 H rosička 7G, 4C 0 5G, 1C 0 rice 8G, 5C 7G, 3C 9G, 7C 9G, 7C šáchor 9G, 4C 9G, 3C 7G 5G hedgehog 10C 9C 9G, 4C 9G, 2C wheat 8C 1C 6G 3G boron - - 0 0 deaf oats 10C 7G, 3C 5G 4G sorghum 10C 9C 7G, 3U 9G, 6U mustard - - 10C 9G, 9C sunflower - - 10C 10G, 9C sugar beet - - 10C 9G, 9C Table F (continued) Leaf part treatment and the soil surface Rate kg / ha Compound 36 0.12 0.06 0.015 soybeans 10C 9G, 9C 9G, 7C Abutilon 10C 10C 8G, 7C Sesbania 10C 10C 10C Cassia 10 C 9G, 3C 8G, 3C cotton 9G, 9C 8G, 8C 4G. 4C povijnice 10C 10C 8G, 4C lucerne 9G 5G, 3C 7G durman 0 0 0 beet 10C 10C 10C maize 2G, 1C 1G, 2C 1G, 1C rosička 5G 0 0 rice 5G 4G 2G šáchor 7G, 5C 7G, 5C 0 hedgehog 9G, 5C 8G, SC 6G, 2C wheat 2G 0 0 bér 3G, 2C 2C 0 deaf oats 3G 0 0 sorghum 7G, 3C 5G, 2C 2G, 2'C mustard 10C 10 C 10C sunflower 10C 10C 1OC sugar beet 9G, 3C 9G, 5C 8G

Table F (continued)

Treatment of leaf part and soil surface

Dose kg / ha Compound 39

0.12 0.06 0.03 0.015 0.015 0.015 0.007 soybeans 10G, 7C 9G, 9C 4G 0 0 3G 0 Abutilon 9G, 7C 8G, 5C 10G, 5C 8G, 4C 8G, 3C 8G, 3C 7G, 3C Sesbania 10C 9G, 4C 10G, 7C 8G, 6C 9G, 4C 5G, 4C 7G, 4C Cassia 9G, 7C 5G, 5C 8G, 5C 5G, 5C 8G, 4C 4G, 6C 5G, 3C cotton 9G, 7C 9G, 6C 9G, 5C 8G, 4C 8G, 4C 8G, 4C 6G, 3C povijnice 9G, 8C 9G, 5C 9G, 4C 9G, 5C 9G, 4C 10G, 3C 9G, 6C lucerne 9G, 8C 10C 9G, 5C 5G, 2C 9G, 5C 7G 7G, 3C durman 0 -. - - 8G 2C -. beet 10G, 7C 10G, 5C 10G, 5C 9G, 5C 10G, 5C 10G, 4C 9G, 4C maize 0 0 3G, 2C 0 1G, 2C 0 2G rosička 0 0 0 0 , 0 0 0 rice 0 0 4G 1G 3G 0 2G šáchor 1G 0 3G 0 0 0 5G hedgehog 0 0 3G 0 0 0 2G wheat 0 0 0 0 0 0 0 bér 0 0 2G 0 2G 0 1G deaf oats 0 0 2G 0 1G 2G 0 sorghum 0 0 5G 0 4G 5G 3G mustard 10C 10C 10G, 5C 10G, 5C 10G, 5C 9G 10G, 5C sunflower 10C 10C 10G. 8G 10G, 8C 10G, 8C 10C 10G, 8C sugar beet 10G, 5C 10C 9G, 3C 10G, 5C 9G, 3C 9G 10G, 4C Test G Dose 0.015

This test shows the herbicidal properties of compound 39 against broadleaf weeds. Approximately 12 soybean plants were grown in a 25 cm diameter plastic container. The following broadleaf plant species were grown in another pot of the same size: sugar beets, Abutilon theophrasti, Sesbania, Cassia, mustard, mulch, alfalfa, durman and beet. The leafy parts of the plants and the surrounding soil were treated with the test compound dissolved in a non-toxic plant solvent by a total spraying rate of 0.015 kg / ha at a plant age of 17 days. Visual evaluation of herbicidal effects was performed 22 days after treatment using the evaluation system described for Test A.

Table G

Batch 0.015

Abutilon 9G, 9C Sesbania 8G, 8C Cassia 7G, 4C mustard 10C povijnice 9G, 9C lucerne 8G, 4C durman 0 beet 10P, 2C

The results show that the test compound is suitable as an excellent post-emergence herbicide against broadleaf weeds in soybean cultivation.

Test H

This test demonstrates the technical progress of the composition of the present invention as compared to the composition of U.S. Patent No. 4,127,405.

soya beans sugar beet

9G

OSOCH ^ H ^ H ^

AND*

SO NHCNH- ~ (O N

₃

SO.CH ^ and ₃ ? N- ( ³ so, nhcnh- ⁾

CHx

Postemergentmě Rate (kg / ha) 0.06 0.015 0.06 0.015 soya 9G, 9C 0 10G, 7C 10G, 7C maize 0 0 10G, 9C 10G, 9U rice 0 1G 9G, 6C 10G, 5C wheat 0 0 6G 5G Abutilon 8G, 5C 8G, 4C 10G, 7C 9G, 5C Sesbania 9G, 4C 8G, 6C 10G, 8C 9G, 3C povijnice 9G, 5C 9G, 5C 10G, 5C 8G, 5C beet 10G, 5C 9G, 5C 10G, 7C —— Pre-emergence Rate (kg / ha) 0.25 0.06 0.125 0.03 soya 4G 3G 8G, 5H 9G, 5H maize 4G 2G 10C 7G rice 0 0 10E 10E wheat 0 0 7G 4G Abutilon 8G, 9C 7G, 3H 9G, 9C 7G, 5H durman obecný 8G, 5C 7G, 3C 9G, 7C 5G povijnice 9G, 3C 9G 9G, 9C 9G, 9C beet 10C 8G, 5H 4G 4G

Claims (15)

Subject What is claimed is: 1. A herbicidal composition comprising as active ingredient at least one compound of the formula (I) EMI2.0 wherein: R 1 is a C 1 -C 4 alkyl group, a trifluoromethyl group or a group of the formula Q is an oxygen atom or an NCH ₃ group, R ₂ is hydrogen, chlorine or methyl, R ₃ represents hydrogen or chlorine, X is methyl or methoxy, Y is a hydrogen atom, a methyl group or a methoxy group and the invention Z is CH, CCl or N, provided that when Y is hydrogen, Z is other than nitrogen. 2. A herbicidal composition as claimed in claim 1, characterized in that it contains at least one compound of the formula I in which R _{@ 1} is C1 -C4 alkyl or trifluoromethyl and the other symbols have the meanings given above. 3. A herbicidal composition as claimed in claim 2, characterized in that it contains at least one compound of the formula I in which R @ ₂ is hydrogen and the other symbols have the meaning given in point 2. Fourth herbicidal composition according to claim 3, characterized in that it comprises as active ingredient at least one compound of formula I wherein R ₃ is hydrogen and other symbols are as defined in point 3. Fifth herbicidal composition according to claim 4, characterized in that it comprises as active ingredient at least one compound of formula I wherein R _t is an alkyl group having 1-3 carbon atoms or trifluoromethyl, Q is O, Z is CH or N and the other symbols have the meaning given in point 4. 6. A herbicidal composition as claimed in claim 5, characterized in that it contains at least one compound of the formula I in which X and Y are each independently methyl or methoxy, phymethyl and the other symbols have the meanings given in point 5. 7. The herbicidal composition of claim 1, wherein the active ingredient is N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate. 8. The herbicidal composition of claim 1, wherein the active ingredient is 2-hydroxy-N- [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide methanesulfonate. 9. The herbicidal composition of claim 1, wherein the active ingredient is N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzone sulfonamide methanesulfonate. 10. The herbicidal composition of claim 1, wherein the active ingredient is N- [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate. 11. The herbicidal composition of claim 1, wherein the active ingredient is 2-hydroxy-N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide. methanesulfonate. 12. The herbicidal composition of claim 1, wherein the active ingredient is N - [(4,6-diimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide methanesulfonate. 13. A herbicidal composition according to claim 1, wherein said compound is N- [(4,6-dimethyl | methoxy-l 3,54riazin-2-yl) - (methyl) aminocarbonyl-2-methanesulfonyl-hydroxybenzensulfonaimid ⁱ phonate. 14. The herbicidal composition of claim 1, wherein the active ingredient is N- [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2-hydroxybenzenesulfonamide-1-propanesulfonate. 15. The herbicidal composition of claim 1, wherein the active ingredient is 2-hydroxy-N - [(4-methoxy-6-methyl-1,3,5-itriazin-2-yl) aminocarbonyl] -benzenesulfonamide-1. -propanesulfonate.