CS200246B2 - Herbicide and process for preparing effective compound - Google Patents

Abstract

1,235,890. m-Anilide ureas and thioureas. STAUFFER CHEMICAL CO. 19 Aug., 1968 [23 Aug., 1967; 19 July, 1968], No. 39583/68. Heading C2C. [Also in Division A5] The invention comprises compounds of the Formula I in which X and Y represent an oxygen or sulphur atom, R 1 and R 4 represent a hydrogen atom or a lower alkyl C 1-6 radical, R 2 and R 3 represent a hydrogen atom or an alkyl, haloalkyl, lower alkenyl C 2-4 , cycloalkyl C 3-6 , 2,4- dichlorophenoxy-methyl carbalkoxyalkyl, naphthyl, phenyl radical or a phenyl radical substituted by a halogen atom or a nitro or lower alkoxy C 1-6 group, R 5 represents a hydrogen atom or an alkyl, lower alkenyl C 2-4 , haloalkyl C 1-6 , cycloalkyl C 3-6 , benzyl or phenyl radical or a phenyl radical substituted by a halogen atom or a nitro, lower alkoxy C 1-6 , or trihalomethyl group, Z represents a halogen atom or a lower alkyl C 1-6 , nitro, amino or trifluoromethyl radical and m is an integer from 0 to 4 with the proviso that when R 1 -R 4 represent hydrogen atoms, X and Y both represent oxygen atoms and m is 0 then R 5 is other than a methyl or ethyl radical. They are prepared by reacting the appropriately substituted mamino substituted anilide with an isocyanate, isothiocyanate or carbamoyl chloride or by reacting an appropriately substituted m-amino substituted urea or thiourea with an acyl halide or acid anhydride. A large number of examples is given. The compounds of Formula I have herbicidal activity.

Description

The present invention relates to a herbicidal composition, the active ingredient of which is a urea derivative.

The present invention provides a herbicidal composition comprising, as an active ingredient, a compound of the formula I *

(I) in which denotes

R ^ is hydrogen or alkyl of 1 to 6 carbon atoms,

R 8 is hydrogen or alkyl of 1 to 6 carbon atoms,

R _{3 is} hydrogen, C 1 -C 10 alkyl, C 2 -C 4 alkenyl, C 1 -C 6 halogenated alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkoxycarbonyl, phenyl optionally substituted with chlorine , nitro or (C 1 -C 4) alkoxy, and naphthyl,

R ^ is hydrogen, alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 4 carbon atoms, halogenated alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, 2,4-dichlorophenoxymethyl, phenyl, optionally substituted with chlorine,

Z is chlorine 0 or 1, wherein when R p is R g, R 4 is hydrogen and m is 0, R ₅ is other than methyl or ethyl.

The compounds of the formula I have both pre-emergence and post-emergence herbicidal activity.

These active compounds are preferably prepared according to the invention by the compound of the formula II

(II) in which

Rp, R, Z and R are as defined above, reacted with a compound of formula III

Cl

(III) wherein

R 8, R 8 are as defined above, in the presence of a hydrogen halide acceptor or, when in the compound of formula I, either Rg or Rj is hydrogen, also with a compound of formula IV

R 4 NCO (IV) wherein

is as defined above.

The following are some examples of the preparation of compounds of Formula I.

Example 1

Preparation of 1- (3'-isobutyramidophenyl) -3-methylurea

12.5 g (0.07 mol) of meta-aminoisobutyranilide are dissolved in 100 cm @ 3 of acetone containing a few drops of dibutyltin dilaurate. Methyl isocyanate (4.4 g, 0.077 mol) was added. The mixture was refluxed for 2 hours. After cooling, the crystalline product is filtered off and dried. Yield: 8.2 g (50% of theory), m.p. 168-171 ° C.

Example 2

Preparation of 1- (3'-pivalamidophenyl) -3,3-dimethylurea

15.4 g (0.08 mol) of meta-aminopivalanilide are dissolved in 100 cm @ 3 of acetone containing 11 g of finely powdered anhydrous potassium carbonate and some powdered copper. Dimethylcarbamoyl chloride (8.6 g, 0.08 mol) was added and the mixture was heated to reflux with stirring for 8 hours. The solid product was filtered off and the acetone was removed under vacuum. The viscous liquid product is triturated with β ether and crystallized. It is washed with water and 5% hydrochloric acid solution and dried. 12.5 g (60% of theory) of the title compound are obtained, m.p. 181-186 ° C.

Example 3 ·

Preparation of 3 ^from -dimethyl -ureido-2,4-dichlorobenzanilide

This compound is prepared by reacting 9.0 g of 2'-aninophen'-dimethylurea with 10.5 g of 2,4-di-tolylortonzoyl chloride in ¹⁰ cm ^{3 of} acetone in ^the presence. 5.5 ^{g of} trietoylamine. ^p o by ^fi ltro-. Purification and washing of the product gave 16.2 g of the title compound, mp 102-107 ° C.

Example 4

Preparation of 3'-propionamidophenyl urea.

^{8.2 g (9, 0} 5 mole) of ^meta-p ro ^p ionamidoani ^where nu ^p is extended orifice. in ^'100 cm ³ of ^of Eden ^eh of ^the mites in ^the YSE ^when n ^y c ^hl orovo ^{says é} metal. In ²⁰ cm ³ of water is ^y. Usti extended ^{P '4,} 1 ^g of AN ^and the ^alkyl raseln ^d · ^s and it is ^{added to} the acid A solution of e. The resulting mixture was maintained at 30-40 ° C for 3 hours. After cooling, the crystals were filtered off and washed with water. Then they are dried under vacuum. 8.9 g (86% of theory) of the title compound are obtained, mp 188-190 ° C.

Example. ’5

Preparation of 1- (3 ^of -butyramidofenyl) .- 3-methylurea ^11, 5 ^g (0.0 ^{7 mol)} of N ^- meta ^{- amino-phenyl-N '-} methylurea. ^d U is the .suspen in 100 cm @ ^{3 H} et ERU and added dropwise 11.1 g anhydride, n-butyric acid containing 5 drops of concentrated sulfuric acid. The mixture was heated to below. reflux condenser for 1 hour. The mixture was cooled and the product was filtered off. It is then washed with dilute 5% sodium hydroxide solution, dilute 5% hydrochloric acid and water and finally dried. 11.2 g (68% of theory) of the title compound are obtained, mp 158-159 ° C.

Example 6 ‘

Preparation of 1- (3'-cyclohexanecarboxamidophenyl) -3-methylurea

11.5 g (0.07 mol) of N-meta-aminophenyl-N'-methylurea are dissolved in acetone containing 7.7 g (0.076 mol) of triethylamine and dropwise. 11.3 g of cyclohexanecarbonyl chloride are added with stirring. The product precipitates from acetone and is filtered off, washed with water and then dried. ^From IS ^Ka is 16.0 ^g (83% of theory) of said ^E sloučení.n ^y, the 190 and ^{1 93} ° C.

)

The following is a table of compounds that were prepared according to the procedures described. The compounds were numbered for identification and accurate labeling.

Compound * 1 R-> ^H > 5 ° C number 1 2 J 5 1 H H CH ₃ ^C 2 ^H 5 175 to 179 2 H CH ₃ CH ₃ c ₂ h ₅ 279.5 to 282 3 H H 3-Cl-phenyl ^C 2 ^H 5 209 to 211 4 H H CH ₃ i-CjK 167 to 171 5 H H ^C 2 ^H 5 i-C 1 169 to 173 6 H H nC ₃ H? ! -С _Л 169-170.5 7 H H i- ^ ^{1 C} 3 ^H 7 168 to 170 8 H H ^C 2 ^H 5 ^C 2 ^H 5 176-177.5 9 H H i- ^C 3 ^H ₇ ^C 2 ^H 5 184 to 185 10 H H η-0 ₃ Ηγ ^C 2 ^H 5 165 to 168 11 H H cyclohexyl ^C 2 ^H 5 178 to 179 12 H H phenyl ^C 2 ^H 5 211 to 212 13 H H 3-NO ₂ -phenyl ^C 2 ^H 5 207 to 209 14 H H ⁿ '^ 4 ^R 9 ^C 2 ^H 5 151 to 154 1.5 H H 3,4-diCl-phenyl ^C 2 ^H 5 167 to 170 16 H H ch ₂ cooc ₂ h ₅ ^C 2 ^H 5 150 to 152 17 H H ch ₂ ch = ch ₂ ^C 2 ^H 5 157 to 160 18 H H ^C 8 ^H 17 ^C 2 ^H 5 151 to 154 19 Dec H H 1 4-OCH ₃ phenyl ^C 2 ^H 5 210 to 211 20 May H H 4-NO ₂ -phenyl ^C 2 ^H 5 215 to 219 21 H H neftyl ^C 2 ^H 5 278 to 272 22nd H H ch ₂ ch = ch ₂ ^i_C 3 ^H 7 175 to 176 23 H H nC ₄ Hg t-c ₃ h ₇ 157-158.5 24 H H cyclohexyl ⁱ - ^C 3 ^H _? 213 to 217 25 H H ^C 8 ^H 17 1-C ₃ H ₇ 134 to 136 26 H H phenyl 221 to 223 27 Mar: H H 3-Cl-phenyl ic ₃ H ₆ 214 to 216 28 H H 3,4-diCl-phenyl ^i_C 3 ^H 7. 218 to 221 29 H H 3-NO ₂ -phenyl ^i_C 3 ^H 7 201 to 203 30 H H ^GH 3 tc ₄ H ₉ 164 to 166 31 H H t-C-jK? tc ₄ H ₉ 179 to 181 32 H H 3-Cl-phenyl tC ₄ H ₉ 218 to 221

5 200246 Compound R in R- ^B 5 ° C number > ⁿ Ž ° ' 33 H CH ₃ CH} ^t_ C4 ^H 9 181 to 186 34 H H CH3 CH ₂ C / CH _3/3 181 to 183 35 H H 3-NO 3 -phenyl ( ': CH2 / CH3 / ³ 174 to 177 36 H CH3 CH3 CC13 169 to 173 37 H CH3 CH3 0F3 178 to 184 38 H CH3 <CH3 133 to 136 39 H CH3 CH3 CH2O-2,4-d1Cl-phenyl 146 to 148 40 H H C ₂ Hp . C / CH _3/3 56 to 61 41 H H nC ₃ H7 c / ch ^ ³ N3 = ^1, 5158 . 42 H H CH ₂ CH = CH ₂ C / CH _3/3 ⁰ n3 '= ^1, 5293 43 H H nC ₄ ^H ₉ C / CH _3/3 n3 ⁰ = 1.5150 44 H H C / CH _3/3 C / CH _3/3 185.5 to 188 45 H H oyclohexyl C / CH _3/3 145 to 150 46 H H CH3 ch / ch ₃ / c ₃ h ₇ 132 to 137 47 H H C ₂ H ₅ OH / CH 3 / O 3 H 7 118 to 122. , 48 H H. n-C3Hy CH / CH ₃ / C 3 H ₇ np ⁰ = 1/5262 49 H H 1-C ^{3 H} ₇ CH / CH ₃ / C 3 H _{7 n} D ° = 1.5078 50 H H CH ₂ CH = CH ₂ CH / CH3 / C-1H 118 to 123 51. H H ш ^- ^ ⁹ CS / CH / Cý / N7 = ¹ 5318 52 H H C / CH3 / 3 .. CH / CH ₃ / C 3 H ₇ 177 to 181 53 H H . CH3 C / CH3 / ₇ 2C3H 146 to 148 54 H H . C ₂ «5 O / CH 2 C 1 H 3 np ⁰ '= 1 ^, 5258'h 55 H H n-C? H? C / CH3 / 2O3H7 n3 ⁰ = 1.5242 56. . H H ¹ -C ^{3 H} ₇ 0/0 ^ / 20387 np = ^{0 1} 5202 57 H H CH ₂ CH = CH ₂ C / CH3 / 2O3H7 n ⁰ = 1 ^, 5455 58 H H nC ₄ Hg , C (CH 3) 2 N7. = ¹ 5075 59 H H oyclohexyl 0/0 ^ / 203 ^ np = ^{0 1} 5409 60 H H, OHgOH / Br / OHgBr C (CH ₂ ) ₂ O ₇ 65 'to 70 61 H H CH3 CH ₂ 01 183 to 188 62 H H CH3 ⁰⁰¹³ 142 to 148 63. H H CH3 0F3 141 to 147 64 H Έ CH3 C / O2H5 / 2 148 to 153

200246 6

Compound number ^R 1 ^R 2 ^R 3 ®5 OF t. te ⁿ D Noc: 2 ° C > 65 H H CH ₃ phenyl 201 to 203 66 H H CH ₃ ch / ch ₃ / c ₂ h ₅ 153 to 159 67 H H 1- ^{с зН} ₇ ch / ch ₃ / c ₂ h ₅ 190 to 192.5 68 H H C / CH _3/3 ch / ch ₃ / c ₂ h ₅ 167 to 172 69. H H CH ₃ CH / CH ₃ / C ₂ H ₅ 6-C1 179 to 183 70 H H ⁱ - ^C 3 ^H 7 ! -С ₃ Н ₇ 6-C1 126 to 128 71 ^C 2 ^H 5 H CH ₃ c ₂ h ₅ 200.5 to 204.5 72 H H ^GH 3 CH ₂ CH ₂ C / CH _3/3 193.5 to 195 73 H H CH ₂ CH ₂ C / CH _3/3 185 to 190 74 H H CH ₃ nC ₃ ^H ₇ 158 to 159 75 H H CH ₃ nC ₄ H ₉ 159.5 to 161 76 H H CH ₃ n- ^c ₅ ^H , j 162 to 163.5 77 H H ^CH 3 CH ₂ CH / CH _3/2 144 to 145.5 78 H H CH ₃ CH ₂ CH ₂ CH / CH _3/2 166 to 167.5 79 H H CH ₃ CH = CH ₂ 160 to 165 80 H H CH ₃ CH = C / CH _3/2 n ³⁰ = ^D 1,5453 81 H H CH ₃ cyclopropyl 197 to 201 82 H H ^CH 3 cyclohexyl 190 to 193 83 H H CH ₃ CH ₂ O-2,4-diCl-phenyl 226 to 231 84 H H H C / CH _3/2 C _{3 H?} 142 to 147 85 H H ^C 2 ^H 5 CH ₂ C / CH _3/3 166 to 169 86 H H nC ₄ H ₉ H 106 to 112 87 H H nC ₄ ^H _g CH ₃ 138 to 141 88 H H nC ₄ H ₉ n-C? H? 139 to 142 89 H H nC ₄ H ₉ CH = C / CH _3/2 68 to 73 90 H H nC ₄ H ₉ CH ₂ CH / CH _3/2 113 to 116 91 H H nC ₄ H ₉ CH ₂ C / CH _3/3 73 to 78 92 H H nC ₄ H ₉ CC1 ₃ 113 to 115. 93 H ^C 2 ^H 5 ^C 2 ^H 5 C / CH 3 / C 1 H 2? n ³⁰ = 1.5648 94 H ^C 2 ^H 5 ^C 2 ^H 5 ° 2 ^H 6 n ³⁰ = ⁿ D 1.5425 95 H ^C 2 ^H 5 H CF ₃ 207 to 211

IN

Compound number ^Й 1 ^й 2 ^Β 3 В ₅ Z t. t. ° c 96 Η ^С 2 ^Н 5 Η СН ₂ СН = СН ₂ 174 to 181 97 Η Η ^С 2 ^Н 5 С / СН _3/2 СН ₂ С1 68 to 72- 98 Η Η ^С 2 ^Н 5 CHCHjCgHj 122 to 126 99 Η Η ^С 2 ^Н 5 СН ₂ СН / СН _3/2 167 to 168.5 100 ALIGN! Η Η ^С 2 ^Н 5 СН / С ₂ Н _5/2 133.5 to 137.5 101 Η Η from _{2 to 5} С / СН ₃ / (СН / СН _3/2) СН / СН _3/3 СН 63 to 69 102 Η Η ^С 2 ^Н 5 СН ₂ СН / СН _3/2 СН С / СН _3/3 71 to 75 103 Η Η 4,4-diClphenyl С / СН _3/3 219 to 210 104 Η 0Η ₃ сн ₃ ^C 2 ^F 5 150.5 to ¹⁵⁷ 105 Η Η с / сн _3/3 ^С 2 ^Н 5 116 to 221 106 Η Η ^сн з с / с н _{2 5/2 3} сн 174 to 175 107 Η Η сн ₃ СН ₂ СН / СН ₃ / С ₂ Н ₅ 139 to 142 108 Η Η ^сн з СС1 ₃ ¹³⁵ to 138 109 Η Η сн ₃ ^C 2 ^F 5 177 to 180 110 Η Η сн ₃ СС1 = СС1 ₂ 195 to 196 111 Η Η сн ₃ СВг / СН _3/2 121 112 Η Η СН ₃ С / СН _3/2 СН ₂ С1 131 to 136 113 Η Η ^сн з СН ₂ СН / СН ₃ / С ₂ Н ₅ 138 to 140 114 Η Η СН ₃ СН ₂ С / СН _3/2 С ₂ Н ₅ 163 to 166 115 Η Η ^сн з СН / С ₂ Н ₅ / С ₄ Н ₉ 162 and ^ 164 116 Η Η ^сн з СН ₂ СН / СН _3/2 СН С / СН _3/3 132 to 135 117 Η СН ₃ СН ₃ СС _{1 2} СН ₃ 155 to 159 ' 118 Η Η ^С 2 ^Н 5 СН ₂ СН / СН ₃ / С ₂ Н ₅ x 136 áž 138 119 ' Η Η from _{2 to 5} СН ₂ С / СН _3/2 С ₂ Н ₅ 137 to 140 120 Η Η ^сн з сн / с н _{5 2/4} н с ₉ 160 to 162 121 Η Η ^С 2 ^Н 5 сн / с н _{5 2/4} н с ₉ 165 to 167 122 Η Η ^сн з СС _{1 2} СР ₃ 151 to 154 123 Η СН ₃ СН ₃ CC1 ₂ CF ₃ 105 to 110 124 Η Η ^С 2 ^Н 5 ^C 2 ^F 5 194 to 196 125 Η Η ^сн з 2-chlorophenyl 155 to 159 126 Η Η СН ₃ 3-chlorophenyl 301 to 305 127 Η Η СН ₃ 4-chlorophenyl 314 to 317

(

Compound number ^{R. R} 2 ^R 3 «5 OF mp ° C 128 H H CH3 2,4-dichlorophenyl 216 to 219 129 H H CH3 3,4-dichlorophenyl 203 to 205 130 H CHj CH ₃ 2-chlorophenyl 101 to 105 131 H CH ₃ CHj 3-chlorophenyl 175 to 178 132 H CH ₃ CH3 4-chlorophenyl 195 when heated quickly 133 H CH ₃ CHj 2,4-dichlorophenyl 102 to 107 134 H CH3 CHj 3,4-dichlorophenyl 96 to 99 135 H CH3 n-C4H ₉ CF3 glassy substance 136 H CH3 nC ₄ H ₉ ^C 2 * 5 105 to 108 137 H CH3 ⁿ -C ₄ H ₉ glassy · substance 138 H CH3 ^nC 4 ^H ₉ t-C4H9 glassy substance 439 H CH3 n-C4H ₉ C / CH _3/3 CH ₂ Cl glassy substance 140 H CH3 n-C4H ₉ ch / ch ₃ / c ₂ h ₅ glassy substance 141 H CH ₃ nC ₄ H ₉ ch / C ₂ H _5/2 glassy · substance 142 H CH3 _n-CH3 СН / СНз / СзН ₇ glassy substance 143 H CH3 n ~ C4H9 t-CH 2 C 4 H 9 glassy substance • 144 ’ H CH ₃ nC ₄ H ₉ phenyl 65 to 68 145 H CH3 nC ₄ H ₉ 3-chlorophenyl 62 to 64 146 H ^CH3 nC ₄ H ₉ 2,4-dichlorophenyl [nu] C-1 ^, 5460 Compounds common formulas I have, as already mentioned, herbicidal efficiency and

useful for controlling the growth of various plant species. Their herbicidal activity was tested as follows:

Pre-emergence herbicide test

The day before the test, the seeds of seven different weed species were planted in individual rows using one species per row across the width of the box. The seeds of the blood-grass (Digitaria sanguinalis / L / scop), the grass (Setaria glauca / L / Beauv.), The hedgehog (Echinochloa crusgalli. / L / Beauv.), The oat (Avena sativa) were used. (L /), GAnaranthus retroflexus (L)), Brassica juncea (L / Coss.) And curly sorrel (Rumex crispus / L).

Enough seed was planted to germinate in the row after application of the composition. 20 to 50 seedlings, depending on the size of the plants. After planting the areas were sprinkled. Spray solution ^if L ^conn Raven extended ^P U ^S subtracting 50 m ^{g s} tested compound in 3 cm ³ of ^solvent, such as acetone, obsahujtoíto 1% Tween ²⁰ ® ^(p olyoxyet ^hy merely sorbitan. Monotourét).

The next day, each box was sprayed with a solution containing 9.072 kg of test compound in 363.672 L of solvent per 0.4 ha.

Sprayers were used to spray the solution onto the soil surface. The boxes were placed in a ^{preheater skl} e p ^{s 26,} 7 ° C and pravidetač bellow. 2a two weeks ^was to ^t ^ ov anoven degree vnění comparing weed germination and growth stage of each weed cartons sprayed weeds in several control boxes without herbicide.

The evaluation system is as follows:

- = no significant damage (0 to 15% effect on growth) + = slight damage (25 to 35% effect on growth) ++ = slight damage (55 to 65% effect on growth) +++ = severe damage or death (85 to 100 % growth impact)

The efficacy index is used to express the overall efficacy on all 7-weed species. It is the sum of positive numbers, so the efficiency index 21 represents the complete destruction of all 7 weed species. The test results are shown in Table II.

Post-emergence herbicide test

Seeds of 5 weed species, namely bloody dew, hedgehog corns, deaf oats, rag mustard and curly pike, and one useful plant, the bean (Phaseolus vulgaris), were planted in boxes as described above in the pre-emergence test.

^The rabbit hutch mesh l b ^{y y} m ^{d y} ST ^E n in the while ^the Lenika. ^22, 2 ° C ^{and 2} ° C for 9.4 ^d and Enna est ^{é o} n ^{y. 10-1} 4 days after planting, when fully developed embryonic kidney bean leaf and which have already begun to form the first trifoliate leaves, the plants were sprayed.

The spray was prepared by dissolving 50 mg of the test compound in 5 ml of acetone containing O 3

1% Tween 20 (polyoxyethylene sorbitan monolaurate) and then .přidáním 5 ^cc of water. The solution was sprayed with a foliage sprayer. The spray concentration was 0.5% and its amount was approximately 22.44 kg / ha when all spraying of the plant and soil was captured, but with some loss of spraying the amount was estimated to be approximately 14 kg / ha.

Beans were used to determine defoliation and affect plant growth. A few days before the test, two or three bean plants were selected per box by cutting off excess weaker plants. The sprayed plants were placed back in the greenhouse and the leaves were not sprayed with water three days after the test. The soil was irrigated with a mild stream of water from the spray hose without wetting the leaves.

Assessment of damage was performed 14 days after the test. The rating system is the same as the preemergence test described above, where (-), (+), (++) and (+++) were used for different assessments of damage and growth. Symptoms of damage have also been reported. The maximum efficiency index in totally influencing the growth of the plants used in the post-emergence test is 18, which is the sum of the numbers. The herbicidal activity indices are shown in Table II.

Table II

Her ^bi c ^{i s} activity days ** - landing tests ^{with E}

Compound Preemergence Postemergence 1 18 18 2 2 0 3 9 1 1 4 21 18

Compound

Přeemergence

Postemergence

Ю 19

21

1211

130

1421

20 May

20 May

Compound

Preemergence

Poatemergence

59 9 13 60 5 12 ⁶¹ 0 4 62 17 18 63 21. 18 64 21 18 65 8 11 66 21 18 67 21 18 68 18 18 69 6 13 70 10 Π 71 5 4 72 17 18 73 4 16 74 15 Dec 18 75 9 18 76 5 14 77 18 18 78 19 Dec 18 79 1 1 1 80 19 Dec 18 81 14 18 82 11 18 83 4 11 84 2 11 85 21 18 86 0 9 87 1 11 88 7 14 89 20 May 17 90 21 18 91 21 18 92 17 14 93 11 16 94 14 18 95 21 18 96 .15 17 97 20 May 18 98 21 18 99 17 18 100 ALIGN! 21 18 101 10 17 102 7 18 103 0 10 104 20 May 18 105 17 18 106 19 Dec 18 107 20 May 18 108 20 May 18 109 21 18 110 0 6 111 21 18 112 21 18

Compound Preemergence Postemergence

113 21 18 114 19 Dec 18 115 19 Dec 18 116 15 Dec 17 117 21 18 118 19 Dec 18 119 16 18 120 16 18 121 12 16 122 19 Dec 18 123 18 18 124 19 Dec 18 125 11 16 126 14 12 127 11 13 128 10 12 129 3 10 130 17 18 131 19 Dec 18 132 17 14 133 18 18 134 5 11 135 21 18 136 21 18 137 21 18 138 21 18 139 21 18 140 21 18 141 21 18 142 21 18 143 21 18 144 - 15 17 145 17 17 146 19 Dec 17

* <21 = 85 to 100% effect on growth of all 7 plant species in preemergence test = 85 to 100% effect on growth of all 6 plant species in postemergence test

As can be seen from Table II, the compounds of formula I are highly effective pre-emergence and post-emergence herbicides. They are equal to the most efficient known urea-based herbicides and, moreover, have a selectivity to weeds, whether broad-leaved or grass-like.

The herbicides of the invention can be applied in different ways at different concentrations. In practice, they are made with an inert carrier in a form suitable for application as powders, sprays, wetting agents and the like. They can be dispersed in water by means of a diluent or can be used in mixtures with organic liquids, in oil-in-water emulsions, water-in-oil emulsions, with or without the addition of a wetting, dispersing or emulsifying agent.

The amount used depends on the nature of the seeds or plants whose growth is to be affected and ranges from about 1 to 5.6 kg / ha. A preferred method of application is a narrow, strip-like line culture.

The herbicides of the invention are applied to plants in a conventional manner. Powders and liquid mixtures can be applied to plants by spraying or spraying. They can also be applied from airplanes as a powder or spray because they are effective in very small doses. To modify and control the growth of germinating seeds or growing seedlings, for example, powders and liquid mixtures are applied by conventional methods and are preferably incorporated into the soil to a depth of at least 1.27 cm below the surface. It is not necessary for the herbicides to be mixed with soil particles · They can only be applied by spraying or spraying on the soil surface.

The herbicides of the invention can also be applied by adding to field irrigation water. This method allows the mixture to penetrate the soil simultaneously with the absorbed water. Powder mixtures, granular mixtures or liquid forms applied to the soil surface may be introduced below the soil surface in a conventional manner such as by stitching, dragging or mixing.

The herbicidal compositions may also contain other additives, such as fertilizers, plant pest control agents and the like, used. as an adjuvant or in combination with any of the above-described compositions. Other herbicides useful in combination with compounds of Formula I include, for example, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid, and salts, esters and amides thereof; triazine derivatives such as 2,4-bis (3-methoxypropyllanino) -6-ethylthio-s-triazine, 2-chloro-4-ethylamino-6-isopropylanino-s-triazine and 2-ethylamino-4-isopropylamino -6-methylmercapto-s-triazine, derivatives. ureas such as 3- (3,4-dichlorophenyl) -1,1-dimethylurea and 3- (p-chlorophenyl) -1,1-dimethylurea, and acetamides such as Ν, Ν-diallyl-alpha-chloroacetamide, N- ( alpha-chloroacetyl) hexamethylenimine and Ν, Ν-diethyl-alpha-bromoacetamide and the like; Benzoic acids such as 3-amino-2,5-dichlorobenzoic acid; thiocarbamates such as S-propyldipropylthiocarbamate, S-ethyldioproplylthi (η 1 β-β-β-β-β-β, S-ethylcyclohexyl thiocarbamate, S-ethylhexahydro-1H-azepine thiocarbamate and the like.

As artificial fertilizers applicable in. in combination with the active compounds according to the invention, for example, ammonium nitrate, urea and superphosphates can be mentioned. Other suitable ingredients include substances in which the plant organism roots and grows, such as compost, manure, humus, sand, and the like.

Claims (4)

A herbicidal composition, characterized in that it contains, as an active ingredient, a compound (I) in which: R, hydrogen or alkyl of 1 to 6 carbon atoms, R 8 is hydrogen or alkyl of 1 to 6 carbon, R 1 is hydrogen, alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 4 carbon atoms, halogenated alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxycarbonylalkyl of 3 to 6 carbon atoms, phenyl optionally substituted with chlorine, nitro or (C 1 -C 4) alkoxy, and naphtha], R 8 is hydrogen, alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 4 carbon atoms, halogenated alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, 2,4-dichlorophenoxymethyl, phenyl, optionally substituted with chlorine, Z is chlorine and m is 0 or 1, wherein when R, R8, R are hydrogen and m is 0, R6 is other than methyl or ethyl. 2. A herbicidal composition as claimed in claim 1, wherein the active ingredient is a compound of the formula I * ( R ^ is hydrogen or alkyl of 1 to 6 carbon atoms, R _{2 is} hydrogen or alkyl of 1 to 6 carbon atoms R 8 is hydrogen, C 1 -C 10 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkoxycarbonyl, phenyl optionally substituted by chlorine, nitro or C 1 -C 4 alkoxy and naphthyl, R 1 is C 1 -C 6 alkyl, C 2 -C 4 alkenyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, phenyl optionally substituted with chlorine, Z is chlorine 0 or 1, wherein when R 1, R ₂ , R 4 is hydrogen and m is 0, R 4 is other than methyl or ethyl. 3. A method for producing an active ingredient of a herbicidal composition according to claim 1 of formula I wherein ^R 1> ^R 2 ^'R 3 * ^R 5' ho II Z and m are as defined in item 1, characterized in that (I) the compound of general formula (II) wherein R 1, R 2, Z and m are as defined above, is reacted with a compound of formula III NC-C1 wherein ^R ₂ and y are as defined above, in the presence of a hydrogen halide acceptor or, if represents the compound of formula I, either R ₂ or R ≠ hydrogen is also a compound of formula IV wherein R ^ is as defined above R ₃ NCO 4. The process of item 3 for producing a compound of formula I * (d) wherein ^R p R 8, ^R ₃ , R 6, Z and m have the meaning given in item 2, characterized in that the compound of formula (II) Rp, R, Z and m are as defined above, reacted with a compound of formula NC-C1 In which R 8a are as defined above, in the presence of a hydrogen halide acceptor or when in the compound of formula (I), they are either of formula (IV) R 8 or ^R ₃ hydrogen, whether or not with a compound R ₃ NCO