RU1836014C - Weed-fighting method - Google Patents

Abstract

 2998259/05 10.23.80 08/15/93. Bull. No. 31 910956; 965070; 015341; 029281 05/30/78; 11/30/78: 03/01/79; 04/13/79 US E.I. Dupont de Nemours & Company (US) George Levitt (US) Netherlands Patent No. 121788, cl. A 01 N 1) / 02. published. 1966. METHOD FOR FIGHTING AN UNWANTED VEGETATION Essence: a soil or plants is treated with a dose of 0.002-4.0 kg / ha of a compound of the formula hekeyl, 2-ethylcyclohexyl, 2-C-cyclohexyl, 3-methylcyclopentyl, cyclohexene-2, CH3CHNOCHOCHASOCHNA. -ch2- (o) 1 С№ СН2СН20С2Н5, adamantyl; if Q is sulfur, then R is methyl, isopropyl, cyclohexyl; if Q is -N-, then R and Re are the same and mean Re methyl, ethyl, allyl, or when Re-H R is C3-C4 alkyl, -2-methylallyl, / CHtCH) -; H rAeR -H.CHa, F, Ci; Rl (

Description

-C-QR

where | RI h A6

X

Emergency &. N4y

 Q is oxygen, sulfur, or NRe,

I and, if Q is oxygen, then R is H, Na, Csb-alkyl, 2-chloroethyl, cyanomethyl, C3 C alkenyl, 2-methylcyclohexyl, 3-methylcyclohexyl. 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 2,6-dimethylcyclo H, CF3, G, F; R111 - H. F, Cl. Br, CN, CF3, CH3, OCH3, NOa, and with Re — CH3, R — C3CH, OCH3. CH (CH3) C s CH, CH2CH2CH3 CH (CH3) 2, CH2CH3, or Rn Re are used together with the formation of (CH2X (CH2) 3 or (CH2) 20 (CH2) 2; R2-H, 5-CI, 5-N02, 5-NH2, 5-OCH3, 5-CH3, 5-SCH3.5-CN, 5-CP3, 6-CI, 3-CI, 5-F or 4-CH3; Pz-H or CH3 ; X-H, CI, CH3, OCH3 OC2Hs; while X and Y are not simultaneously equal to N. Y-H, Ct-C3-alkyl, O-StC3-alkyl, OCH2CH CH2, OCH2C and CH, OCH2CH02CH2CH2CH, OCH (CH3) CO2CH3, CH20Cl-C2-alkyl, OCH2CF3. OCH2CH2F, CFs, CHF2, OCH2CH2SC CH2CI, Cl, OCH2CH2CN, NHCH3. N (CH3) CH2CN, N (CH3) OCH3. N3,

M (CH3, SCH3. SCN. NO, 0 (CH2) zOC2H5: aZ-CH or N. 12 tab.

(L

WITH

00 GJ O O

Ј

 Oj

; The invention relates to a method for controlling 6M against undesirable plants using N- (reTepoiiHiaiM4ecKHx amino carbonyl) arylsulfonamides.

The compounds used in the method are useful substances for agricultural use, for example, by plant growth regulators and herbicides.

The aim of the invention is to increase the efficiency of the method.

The goal is achieved in that in the method of controlling undesirable vegetation by treating the soil or plants with N-re-cyclic aminocarbonylarylsulfonamide, the compound of the general formula is used as the latter

O-C-Q-R

RV SO HC-N- O R3

where P1's V

N-y

cho; g,

Q is oxygen, sulfur or NRe, provided that if Q is oxygen, then R is H, Na, Ci-Cs alkyl, 2-chloroethyl, cyanomethyl, C3 C4 alkenyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 2-ethylcyclohexyl, 2-C-cyclohexyl, trimethyl-cyclopentyl, cyclohexene-2, CH2CH2OCH2CH2Cl1,

CH (CHe) CHg - © -, CH2CH20C2H5 or

adamantyl, if Q is sulfur, then R is. methyl, isopropyl or cyclohexyl, if Q is NRe, then R and Re are the same and mean methyl, ethyl, allyl, and when RS is H, R is Cz C4 alkyl, 2-methylallyl, cyclopropyl, cyclohexyl,

CH (CH3CH § V;

where R is N. CHs, F or

R is N. CPz, CI or F;

 And, F, CI. In the city of CN, SRz, CHz, OCHz or N02,

or, if Re is CH3, then R is C3CH, OCH3, CH (CH3), CH2CH2CH3, CH (CH3) 2, CH2CH or R and Re taken together can form the group (CH2X (CH2) s or

(CH2) 20 (CH2) 2:

R2 is H, 5-Ci. 5-N02, 5-NH2, 5-OCH3, 5-CHCH, 5-CN, 5-CF3. 6-CI, 3-CI, 5-F, 4-CH3, 5-CH3:

Yaz-N or CHz;

X is H, CI, CH3, OCH3, OC2H5, while X and Y are not simultaneously equal to H;

Y is H, Ci-C3-alkyl, 0-C1-C4-alkyl, OCH2CH CH2, OCH2O CH, OCH2CO2CH2CH2CH, OCH (CH3) CH2CH. CH2OC1-C2-alkyl, OCH2CF3, OCH2CH2F. CF3, CHF2, OCH2-CH2CI, CH2CI, CI, OCH2CH2CN,

INSNs, N (CH3) CH2CM, NO 0 (CH2) zOC2H5,

Z-SNily, at a dose of 0.002-4.0 kg / ha. Compounds of this formula are prepared by reacting the corresponding substituted o-carbonylbenzenesulfonylisocyanate or isothiocyanate with a suitable aminopyrimidinomino or aminotriazine.

Useful preparations based on compounds of this formula that can be used in the process are prepared by conventional methods. These include perfumes, granules, tablets, solutions, suspensions,

emulsions, wettable powders, emulsifiable concentrates and the like. Many of them can be applied directly. Aerosol preparations can be filled using conventional media and work with

in volumes of the order of several liters - several hundred liters per hectare. Highly concentrated formulations are initially used as intermediates for the preparation of the corresponding formulation formulations. The latter usually contain about 0.1-99 wt.% The active principle, and at least (a) about 0.1-20% of one or more surfactants and (b) about 1-99%

solid or liquid diluent;

Table 1 gives the components in an approximate ratio ..

. Depending on the purpose and physical properties of the compound, the content of the active substance. The beginning may be different. A higher ratio of surfactant to active principle is achieved by adding it to the composition or by mixing it into a treatment tank.

More adsorbent diluents are preferably used for wettable powders, denser for dusts. For β-suspension concentrates, solubility below

0.1%; it is preferred that the KOH4eHTpaYbt solutions are resistant to phase degradation at 0 ° C.

Preparations may contain fewer additives to reduce foaming, sintering, corrosion, microbiological growth, etc.

: Methods for preparing such formulations are well known. Solutions are obtained by simple mixing of the components. Thin microliters are obtained by crushing on a hammer mill or a mill operating on a liquid medium. Suspensions are obtained by wet crushing. Granules and tablets are prepared by applying the active compound from prepared carrier granules by agglomeration. The herbicide compounds used have a high degree of pre-emergence inhibition of weed growth in cases where complete inhibition of the growth of the entire vegetation is required. For suitable dosages and times of use, the method of the invention can be used to control plant growth and to selectively treat weeds in crops such as wheat and barley.

: The exact amount of the compounds used in the process varies depending on the desired effect, the amount of foliage, the type of weed suppressed, the type of crops, the type of soil, the composition and the application, weather, etc. Since so many variables play a role, it is not easy to determine the dosage for use under various conditions. In general, these compounds are used in amounts of p, 002-4.0 kg / ha, preferably 0.125-4JO kg / ha. In addition, higher amounts of compounds within this range are used for weeds or to increase soil resistance, and lower doses are used to selectively inhibit weed growth in crops.

; By combining the compounds of said frmule with known herbicides, effective control of tafa-weeds in low crops, such as wheat and barley, is also achieved. Typical herbicides for use are 3- (3-chloro-4-methylphenyl) -1,1-d-methylurea chlortoluron. MCPP G (±) -2 (4-chloro-2-methyl-phenoxy) propapovic acid, mtoxuron 3- (3-chloro-4-methoxy-phenyl) -1,1-dimethylurea, metabemzthiazuron 1- (b | benzotizole -2-yl) -1,3-dimethylurea, dichloropop (methyl-2-4- (2,4-dichloro-phenoxy-c) phenoxy propanoate, tri-aplate (S-2,3-dichloroallyldiisopropylthiocarbamate), and oprsturon 3 - (4-isopropylphenyl) -1,1-, g; i-methyl-urea or diphenoxyquat ion 1,2-dimethyl-3,5-diphenylpyrazole -.

The compounds may also be used in combination with other herbicides, preferably together with ureas.

for example 3- (3,4-dichlorophenyl -1,1-dimethyl urine in another, 3- (3,4-dichlorophenyl) -1-methoxy and-1-methyl urine in urine

1,1-dimethyl-3- (a, a., A-trifluoro-t-tolyl) urea, triazines, for example 2-chloro-4- (ethylamino) -6- (isopropylamino) -5-triazine, uracils for example 5-bromo-3-sec-butyl-b-methylura-cycl, H- (phosphonmet and l) glycine.

3-cyclohexyl-1-methyl-6-dimethyl-amino-5-triazin-2,4 (1H, 3H) -dione, N, N-dim8-ethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid (and neighboring compounds), 4-chloro-2-butynyl-3-chlorophenylkzrbamate, diisopropylthiol carbamic acid, 5- (2,3,3-trichloroallyl) ether, ethyl N-benzoyl-M- {3,4-dichlorophenyl) - 2 - a and m and about p and p about about n and t about m, 4-amino-b-tert-butyl-3 (methylthio} -1,2,4-triazin-5 (4H) -on-ohm, 3 -isopropyl-1H-2,1,3-benzothiodiazine- (4) -ZH-one-2,2-dioxide, a, a, a-trifluoro-2,6-diitro-M, M-dipropyl-p-toluidine 1,1-dimethyl-4,4-bipyridinium ion,

monenzril megenarsonate and 2-chloro-2, 6-distyl (methoxymethyl) -acetanilide.

The proposed method was tested in the greenhouse and on the site. The method was evaluated on the following scale: 0 - no effect, 10 - full effect; the symbols shown in the tables have the following meanings: C - chlorosis or necrosis; D - leaf fall; E - inhibition of seedling; G - growth retardation; N - molding

effects U - extreme pigmentation; 6Y - falling buds or flowers.

PRI me R 1. No.- (4,6-Dimethylpyrimidin-2-yl) emipocarbonyl -2-methoxycarbonylbeksolsulfonamide.

To 37 g of 2-amino-4, b-dimethylpyrimidine in 500 ml of anhydrous acetonitrile, 67 g of 2-methoxycarbonylbenzenesulfonylisociapot was added with stirring at room temperature. Stirring is continued for 16 hours, then filtered to remove the desired product, which precipitates as a white solid with mp. 198-202 ° C. IR Absorption Peaks 1750, 1700, 1600, and 1550

match the desired compound. Note 2. M- (Methoxy-b-methyl-1,3,5.-trizzin-2-nl) aminocarbonyl -2-methoxycarbonplbemzolsulfonamide.

To an anhydrous suspension of 1.4 g of 2-amino-4-methoxy-b-boiler-1, 3,5-triazine in 25 ml of methylene chloride was added at room temperature and a pressure of 2.4 g of 2-methoxycarboxylbepzolsulfonylisocyanate. The mixture was stirred for 1G h and filtered. Filtrate

evaporated to dryness, the residue was triturated with butyl chloride and the product was isolated by filtration. The latter has a so pl. 165 ° C. and IR absorption peaks of 1550, 1600, 1680 and 1700 NMR spectrum: 2.5.3.65.4.0 with aromatic multiplet 7.2-8 ppm;

Using the methods of Examples 1-2 with equivalent amounts of suitable 2-amino-1,3,5-triazines and correspondingly substituted sulfonyl isocyanates or isothiocyanates, the compounds shown in Tables 2 and 3 can be obtained, where + is marked with compounds that are not enter into the interest for the vital, because not shown to be sufficiently effective in testing.

Tests were carried out using the following procedures.

PRI me R A. Plant seeds Digitarla spp; Echlnochloa crusgalli; Avena fotua; cassia tora; Ipomoea spp., Xanthlum spp., Maize, sorghum, soybeans, rice, wheat and tubers Cyperus rofundus are seeded in the plant medium and treated with a non-phytotoxic solution of the compounds according to table XII in a solvent before germination. At the same time, the same seeds and tubers of all these plants are sown as a control. Control vessels are not treated, i.e. do not contain any compounds or solvents. At the same time, cotton with 5 leaves (including cotyledon), a bush fal with a third three-leafed, blooming leaf, Dig taria spp. with 2 leaves, Echlnochloa crusgalli with 2 leaves, Avena fatua with 2 leaves, Cassia tora with 3 leaves (including cotyledon), Ipomoea spp. with 4 leaves (including cotyledon leaves), Xanthium spp. with 4 leaves (including cotyledon), sorghum with 3 leaves, corn with 4 leaves, soy with 2 cotyledon leaves, rice with 3 leaves, wheat with 1 leaf and Cyperus rotundus with 3-5 leaves are pollinated non-oil a toxic solution of the compounds according to table XII in a solvent. Other groups of all the same plants are treated with the same non-phytotoxic solvent as a control. The plants treated before and after germination and the control are placed under greenhouse conditions for 16 days, after which they are compared with their respective control specimens and the reaction to the treatment is visually determined.

Example B. Two globular vegetation vessels are filled with fertilized soil to which the dusty loam of Fallslngton silt loamsoil has been added. Corn, sorghum, Kentucky bluegrass and various weeds are sown in one vessel. In the second - soybeans, Cyperus rotundus and various

broadleaf herbs. The following grasses and broadleaf weeds are sown: Digitarla sangulnalis; Echinochloa crusgalli; Avena fatua; Sorghum halepense; Setarla faberll; Paopalum dilatatum; Bromus secalinus; Brasslca arvensls; Xanthium psnnsyivanicum; Amaranthus retroflexus; Aeschymene virginica; Ipomoea hederecca; Cassia tora; Slda spinosa; Abutllon 0 theophrastl; Datura stramonium.

The smaller vessel is filled with the treated soil and the rice and wheat seedlings are placed in it, in another small vessel-seedlings of sugar beets. The four vessels mentioned are treated before germination with non-phytotoxic solutions of the compounds of the invention, for example by spraying the surface of the soil until seedlings develop. Appropriate vessels were used in the same experiments without treatment for comparison.

After 4 weeks, the treated and control plants were evaluated. Vessels filled with clay sandy soil Falislngton silt loam are sown with 5 seeds of soybean, cotton, alfalfa, corn, rice, wheat, sorghum and weeds Abutulon theophrasti, Sesbania exaltata, Cassia tora, Ipomoea spp., Dathantram penma, penmatula penmatium penum stantum ., Cyperus 0 rotundus, Echinochloa crusgalli, Setarla faberil, Avena fatua.

After about 2.5 weeks, young plants and the soil surrounding them are sprayed on all sides with the compound of Table X dissolved in a non-phytotoxic solvent. Other groups of the same plants (all) are sprayed with the same non-phytotoxic solvent to obtain control plants. After 2 weeks after treatment, all 0 treated plants are compared with controls treated with a non-phytotoxic solvent and the treatment response is visually determined. It should be noted that wheat exhibits 5 compatibility with several compounds.

Accepted abbreviations of the tested species: NUT NUTSEDGE - sedge of walnut CRB - CRABGRASS - dewdrop

CAS - CASSIA - Cassi 0 TEA - TE AWE ED - brisket

RAP-RAPE-rapeseed

JMW-JIMSON WE ED-Smelly Datura VEL - VELVETLEAF - Rope of Theophrastus BKG BLACKGRASS - Mouse Foxtail 5RCE-RICE-Rice

SBT SUGAR BEETS - sugar beet

WHT - WHEAT - Wheat

WIO WILD OATS - wild oats

CKL COCKLEBUR - the cockock

MOG MORNINGGLORY - MILF

SOT - COTTON - cotton iJNG JOHNSONGRASS - sorghum Aleppo i BYG BARNYARDGRASS - millet rooster i GFX GIANT FOXTAIL-foxtail ISON .SOYBEAN-со

ICRN - CORN - Corn

j Prototype compound 1

.CHa OCT

II

SOoNHCN- O; N

AN4NH4

Compound Prototype 2

  © ,. N / 1

S02NHCN- C5N

L nhk

Claims (1)

1.С.8С -1С.4С 8С 1С.8С 10Е 5С.9Н 2С, 70 90 9И 9С 9С 9S 9S YUS .. YUS 9S YUS YUS YUS YUS 9S YUS toe 9C 7C.9C 1C, W 9g 9H 9B 5C.9G UE 5S.L1 5C.9G 90 9U 5C.9G UE 9C 6C.9C 9C US 9C US 9C 9C toe 9C US US 9C 9C 7C, B 10.90 8H 90 ZS.9S UE 3C.9II 3C.9G 90 811 2C.9G UE 9C "S.9C 2C.9C 70.9C 6C.9C "WITH ss.aa 6C.9C 9C 1C 9C 2C 9C 2C.5C 10.90 2C.7C 1C.2H SG 8C UE 6C.9H 2C 90 9H 70 90 9C 2C, 2H, 90 9C 30.9V 2H.8C ABOUT ABOUT 6C.9C 8B 1 S.ZS 9C 1C 1C.4G ABOUT ЗС, bС 1C.8G 1С.1Н ss ace 9H 4C.8G ABOUT as an 70 80 00 so o oh with N3 I After germination IOC 9C IOC 8G .8G 9C 2C.8G 9g 8g "C, 9" 5C.9C. 9C 5C.9G 9C 9C 9G SH 5C.9G toe ac 5C, H IOE 4C.9H 9H 5C.9H 3C.7H IOE SC.9H IOE 9g After sprout Beans bush Cotton plant Sorghum Corn Co Wheat Ovsyug Rice Millet rooster Rosichka Ipomoe Dornishnik Cassi Sedge nut Beet sugar Dog Sunflower Sorghum Corn Co Wheat Ovsyug Rice Millet rooster Rosichka Ipomoe Dornishnik Cassi Sedge nut Beet sugar The data obtained in the test of example A. 9C 5C.9G 2C, 8G 9U.9G 5C.9G 1C.5G 2C.6G 3C.8G 5C, 9H. 2C.7G 9C 9C USUS 9H 2C, 9G 9H 8g 1C.8G 10E 2C.9H 7g 9g 9g 9g IOE mode conditions After sprout Beans bush Cotton Ipomne Orekhova sedge Rosichka Millet rooster Oats empty Wheat Corn So Rice Sorghum Before the shoot, Ipomoe, the Cockerel Cassi Orekhova sedge Rosichka Millet rooster Oats empty Wheat Corn g So Rice Sorghum -. 9H 9C 9C US 9C 9C 9C 9C US 9C 9C 9C 6C, 9G US US 9g 9g 9g 10E 9g 911 ZS.9N 9H UE 9H 10 UE Compound 314 Compound 318 Mp 1b7-170 ° C I .coz (CK2) 2ci crt. After shoot . With 10G, 9C10G, 9C Limnocharis-IOC Sesbani US10C Canadian Casing IOC10C, 9C Cotton 10G, 9C10G.8C Ipomoe IOCIOC Sugar Dope 10G.8C10G, 5C FruityUSYUS Corn10G, 3C10G, 3H Rosichka3GО Rice 7G4G Walnut sedge 9G, 4C5G Millet rooster 8G6G Wheat Foxtail3GО Oats empty5G3G Sorghum IOC10G, 3H Compound 319 Compound 321 .CSCH "JHj 2 SOjHHCHH-rt 322  . “CH2 2dccH2) 2ci CH K l about so2nHcimConnection 323 3 .0 SOjNHCNH Compound 324 CO, CH3 SWG about OSI S02NHCNH4O) , Compound 325 COjiCHj GOT .0 N.OCH, V SO, NHCNH- CO Compound 326 union U11 Union 328 union 329 SOGCH3 @ C9, S02NHCNH4O) N tNCCHy D2NWI OSNE N4ch SD NHCNH- Och CO, CH3 C§CЯ 50ZNHCNH4O} N N H (CHe) g SOGSNu; : nrlgr -0 N4CH3 F3C 4 4SOlNHCNH-g Ochjchj 143-y6 Yz-y 144-176 200-203 OSI 185-189 N OSNE 162-165 198-200 172-17 Compound 330 togetherness 331 Union 332 DOS U N- 3 COCHCH3 SOiNHCN- 6} , @; С02СНЬ н, SOZNHCNH4 N: OCH2CF3 SOOS,  . OCH, CH, , N4 2 3 SO NHCNH O N CH3 Compound 333 Compound 33 ChZZ connection 5 Compound 336 Compound 337 Compound 338 Compound 165-167 DOS U N- 3 3 165-168 170Г1 2 SI : V I3 ockkH  / H S02lJHCNH f) H. M  3 AXIS, /-1 Q . about 1W S02MHCNnXTj) big. co2c "(ai3) 2 o ABOUT axis. 50.1 TISSH6. Tople., With glass 200-203 192-195 CH-. С ° 2С 3bССОСО СН, About „/ 23 EOjNHCNH About 1L / si. gos. Y2-Y5  S02SP2S 2OS2N5 SI, 123-127 VSO2NI CMH (() H 0 , sogsy3 182-18 1 .pr. Consumption rate (kg / ha) 0, After germination From 9 Limnocharis9G Cassie 9g Cotton 9G Ipomoe 9G Sugar Dope 9G Gooseberry 9G Corn9G Rosichka2G Figure 9G Sedge nut SG Millet rooster 9G Wheat7G Foxtail SG Oatsyug6G Sugar Beet 9G 0,062 YUS YUS YUS YUS 9G.8C YUS YUS 9G.40 3C.9G YUS YUS G.4C G G.6C US 0.004 10C.8G 3G 8g 10C.3G 5G, 3C 8G.4C 6G6G .2C ABOUT SC, 8G 6G 3G 4G 3G 7G. schz with oz o N3 O