JPH06172322A - New cycloalkanecarbonyl derivative and herbicide comprising the same a active ingredient - Google Patents

Abstract

PURPOSE:To obtain a new cycloalkanecarbonyl derivative, having a wide herbicidal spectrum and a strong herbicidal activity and useful as an active ingredient of a herbicide having high safety for a certain kind of useful crop. CONSTITUTION:This compound of formula I [X is H or halogen; R<1> is methoxy or halogen; R<2> is H, its agriculturally permissible salt or alkyl; A is NR<3>Y or OR<4> (Y is H, alkyl, alkenyl, alkynyl, cycloalkyl, substitutive aryl, substitutive aralkyl, substitutive 5- to 6-membered heterocyclic group; R<3> is H or alkyl; R<4> is alkyl, alkenyl, substitutive aryl or substitutive aralkyl); (n) is 0-3], e.g. 1-[1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)cyclopentanecarbonyl]-3- methylurea. The compound of formula I (I-a) in which A is NR<3>Y and both R<2> and R<3> are H is obtained by reacting an amide derivative of formula II with a substituted isocyanate of formula III.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel cycloalkanecarbonyl derivative or a salt thereof which has not been described in the literature, and a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art JP-A-3-128632 describes an alkanoic acid containing a pyrimidine ring and a herbicide containing the same.

[0003]

However, the compounds described in the above-mentioned documents have many points to be improved in terms of herbicidal spectrum, dosage amount, selectivity and the like. The present inventors have conducted extensive research to develop a compound having a wide herbicidal spectrum, a high herbicidal effect, and excellent safety for crops, and as a result, the halogenated cycloalkanecarbonylurea derivative of the present invention is novel, and this compound is The present invention has been completed by finding that not only annual but also perennial weeds have an excellent herbicidal effect and that they are highly safe for certain crops.

That is, the present invention has the general formula (I)

[0005]

[Chemical 3]

[Wherein X represents a hydrogen atom or a halogen atom, R ¹ represents a methoxy group or a halogen atom,
R ² represents a hydrogen atom or an agriculturally acceptable salt thereof or a lower alkyl group, A represents a group —NR ³ Y or a group —NR ³ Y
Represents OR ⁴ (wherein Y is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or In each case, it represents a 5- or 6-membered heterocyclic group which may be optionally substituted with a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, R ³ represents a hydrogen atom or a lower alkyl group, and R ⁴ Represents a lower alkyl group, a lower alkenyl group, an optionally substituted aryl group or an optionally substituted aralkyl group), and n represents an integer of 0 to 3. ] The present invention provides a herbicide containing a novel cycloalkanecarbonyl derivative represented by the formula [1] as an active ingredient.

[0007]

The compound of the present invention has the following general formula (I):

[0008]

[Chemical 4]

[Wherein, X represents a hydrogen atom or a halogen atom, R ¹ represents a methoxy group or a halogen atom,
R ² represents a hydrogen atom or an agriculturally acceptable salt thereof or a lower alkyl group, A represents a group —NR ³ Y or a group —NR ³ Y
Represents OR ⁴ (wherein Y is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or In each case, it represents a 5- or 6-membered heterocyclic group which may be optionally substituted with a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, R ³ represents a hydrogen atom or a lower alkyl group, and R ⁴ Represents a lower alkyl group, a lower alkenyl group, an optionally substituted aryl group or an optionally substituted aralkyl group), and n represents an integer of 0 to 3. ] It is a novel cycloalkane carbonyl derivative or its salt represented by these.

X and R in the general formula (I)¹, R²
And R in A³, Y and R^FourIn the definition of
Specific examples of each group are shown below.Halogen atom; Fluorine, chlorine, bromine, iodine,Lower alkyl group; For example, methyl, ethyl, n-pro
Pill, isopropyl, n-butyl, isobutyl, sec-bu
Lower alkyl having 4 or less carbon atoms such as tyl and t-butyl groups
Base, Lower alkenyl group; For example, vinyl, allyl, 3-bu
Number of carbon atoms such as tenyl and 1-methyl-2-propenyl group
A lower alkenyl group of 4 or less,Lower alkynyl group; For example, 2-propynyl, 2-bu
A lower alkyl group having 4 or less carbon atoms, such as a tinyl or 3-butynyl group.
A quinyl group,An optionally substituted aryl group; For example, pheny
Ru, naphthyl, 2-bromophenyl, 3-bromophenyl
Ru, 4-bromophenyl, 2-chlorophenyl, 3-ku
Lolophenyl, 4-chlorophenyl, 2-methylpheny
, 3-methylphenyl, 4-methylphenyl, 2-me
Toxyphenyl, 3-methoxyphenyl, 4-methoxy
Phenyl, 2-nitrophenyl, 3-nitrophenyl,
4-nitrophenyl group, etc.An optionally substituted aralkyl group; For example, Benji
2-bromobenzyl, 3-bromobenzyl, 4-bu
Lomobenzyl, 2-chlorobenzyl, 3-chlorobenzyl
L, 4-chlorobenzyl, 2-methylbenzyl, 3-me
Cylbenzyl, 4-methylbenzyl, 2-methoxyben
Zyl, 3-methoxybenzyl, 4-methoxybenzyl group
etc,Lower cycloalkyl group; For example, cyclopropyl,
Clopentyl, cyclohexyl, cycloheptyl group, etc.Hydrogen atom, halogen atom, alkyl group, alkoxy group
A 5- or 6-membered heterocyclic group which may be substituted; Was
For example, 2-pyridyl, 3-pyridyl, 4-pyridyl,
3-pyrazolyl, 1,2,4-triazol-3-i
2-pyrimidinyl, 4,6-dimethoxy-2-pyri
Midinyl, 4,6-dimethyl-2-pyrimidinyl, 4-
Methyl-6-methoxy-2-pyrimidinyl, 4-chloro
-6-methoxy-2-pyrimidinyl, 1,3,5-tri
Azin-2-yl, 4,6-dimethoxy-1,3,5-
Triazin-2-yl, 4,6-dimethyl-1,3,5
-Triazin-2-yl, 2-thiazolyl, 1,3,4
-Thiadiazol-2-yl group, etc.,Agriculturally acceptable salts; For example, sodium, cariu
Inorganic salts of magnesium, calcium, iron, magnesium, etc .; Ammo
Nium, methyl ammonium, ethyl ammonium, n
-Propylammonium and its isomers, n-butyl
Ammonium and its isomers, n-pentyl ammonium
Um and its isomers, n-hexyl ammonium and
And its isomers, n-heptyl ammonium and its variants
N-octyl ammonium and its isomers, n
-Nonylammonium and its isomers, n-decylurea
Ammonium and its isomers, diethylammonium,
Organic amine salts such as triethylammonium;
It

The groups not specifically shown in the above groups are selected from the above atoms and groups in any combination or in accordance with the generally known common sense. In the above general formula (I) of the present invention, n is 0 or 1 and R is
¹ is a methoxy group, R ² is a hydrogen atom, X is fluorine, A is a group —NR ³ Y (wherein Y is hydrogen or an aryl group, and R ³ is a hydrogen atom). ),
Particularly preferred are the compounds

Of course, it should be understood that the stereoisomers (diastereomers and enantiomers) of the compounds represented by the above general formula (I) are within the scope of the present invention.
Here, when based on the 1-position -CONR ² COA cis- 2-position compound substituent take cis-configuration when a reference group, also 1-position -CONR ² COA group of the general formula (I) A compound in which the 2-position substituent has a trans configuration is called a trans form.

Among the compounds of the present invention represented by the general formula (I), the following general formula (I-1)

[Chemical 5]

The compounds represented by the following general formula (I-2) are shown in Table 1.

[Chemical 6]

The compounds represented by the following general formula (I-3) are shown in Table 2.

[Chemical 7]

The compounds represented by the following general formula (I-4) are shown in Table 3.

[Chemical 8]

The compounds represented by the following general formula (I-5) are shown in Table 4.

[Chemical 9]

The compounds represented by the following general formula (I-6) are shown in Table 5.

[Chemical 10]

The compounds represented by are shown in Table 6, respectively. The compounds described here all represent the trans form.

[0020]

TABLE 1 Table 1 Compound No. n X Y 1001 0 F hydrogen 1002 0 F methyl 1003 0 F Ethyl 1004 0 F n-propyl 1005 0 F isophthalic ° propyl 1006 0 F n-butyl 1007 0 F isophthalic Bu chill 1008 0 F sec-butyl 1009 0 F t-Butyl 1010 0 F Binyl 1011 0 F Allyl 1012 0 F 3-Bethenyl 1013 0 F 1-Methyl-2-prophenyl 1014 0 F 2-Prophenyl 1015 0 F 2-Butyl 1016 0 F 3-Butyl 1017 0 F Phenyl 1018 0 F Naphthyl 1019 0 F 2-Bromo-phenyl 1020 0 F 3-Bromo-phenyl 1021 0 F 4-Bromo-phenyl 1022 0 F 2-Chlorophenyl 1023 0 F 3-Chlorophenyl 1024 0 F 4-Chlorophenyl 1025 0 F 2-methylphenyl 1026 0 F 3-methylphenyl 1027 0 F 4-methylphenyl 1028 0 F 2-methoxyphenyl 1029 0 F 3-methoxyphenyl 1030 0 F 4-methoxyphenyl 1031 0 F 2-nitrphenyl 1032 0 F 3-nitrphenyl 1033 0 F 4 -Nitorphenyl 1034 0 F Benzyl 1035 0 F 2-Blomobenzene 1036 0 F 3-Blomobenzene 1037 0 F 4-Blomobenzene 1038 0 F 2-Chlorobenzene 1039 0 F 3-Chlorobenzene 1040 0 F 4-Chlorobenzene 104 1 0 F 2-Methylbenzene 1042 0 F 3-Methylbenzene 1043 0 F 4-Methylbenzene 1044 0 F 2-Methoxybenzyl 1045 0 F 3-Methoxybenzyl 1046 0 F 4-Methoxybenzyl 1047 0 F Cyclopropyl 1048 0 F Cyclopentyl 1049 0 F Cyclohexyl 1050 0 F Cycloheptyl 1051 0 F 2-Pyridine 1052 0 F 3-Pyryl 1053 0 F 4-Pyrrol 1054 0 F 2,3-Polarryl 1055 0 F 2,3,5-Triazolyl 1056 0 F 2- Primydinyl 1057 0 F 4,6-Dimethoxypyrimin-2-yl 1058 0 F 4,6-Dimethylpyrimin-2-yl 1059 0 F 2-Methoxy-4-methylpyrimidin-2-yl 1060 0 F 2-Chloro-4-methoxypyrimidin-2-yl 1061 0 F 1,3,5-triazine 1062 0 F 2,4-Dimethoxy-1,6 3,5-triazin-2-yl 1063 0 F 2,4-Dimethyl-1,3,5-triazin-2-yl 1064 0 F 2-thiazolyl 1065 0 F 1,3,4-thiadiazol-2-yl 1066 1 F Hydrogen 1067 1 F Methyl 1068 1 F Ethyl 1069 1 F n-Propyl 1070 1 F Isopropyl 1071 1 F n-Butyl 1072 1 F Isobutyl 1073 1 F sec-Butyl 1074 1 F t-Butyl 1075 1 F Vinyl 1076 1 F Allyl 1077 1 F 3-butenyl 1078 1 F 1-Methyl-2-propylenyl 1079 1 F 2-Propenyl 1080 1 F 2-Butyl 1081 1 F 3-Butyl 1082 1 F Phenyl 1083 1 F Naphtyl 1084 1 F 2-Bromo- Phenyl 1085 1 F 3-Bromo-phenyl 1086 1 F 4-Bromo-phenyl 1087 1 F 2-Chlorophenyl 1088 1 F 3-Chlorophen 1089 1 F 4-chlorophenyl 1090 1 F 2-methylphenyl 1091 1 F 3-methylphenyl 1092 1 F 4-methylphenyl 1093 1 F 2-methoxyphenyl 1094 1 F 3-methoxyphenyl 1095 1 F 4-methoxyphenyl 1096 1 F 2-Nitorphenyl 1097 1 F 3-Nitorphenyl 1098 1 F 4-Nitorphenyl 1099 1 F Benjyl 1100 1 F 2-Blomobenzyl 1101 1 F 3-Blomobengal 1102 1 F 4-Blomobengal 1103 1 F 2- Chlorobenzene 1104 1 F 3-Chlorobenzene 1105 1 F 4-Chlorobenzene 1106 1 F 2-Methylbenzene 1107 1 F 3-Methylbenzene 1108 1 F 4-Methylbenzene 1109 1 F 2-Methoxybenzyl 1110 1 F 3-Methoxy Bengal 1111 1 F 4-Methoxybenzil 1112 1 F Cyclopropyl 1113 1 F Cyclopentyl 1114 1 F Cyclohexyl 1115 1 F Cycloheptyl 1116 1 F 2-Perigel 1117 1 F 3-Perigel 1118 1 F 4-Perigel 1119 1 F 2,3-Polasolyryl 1120 1 F 2,3,5-Triazolyl 1121 1 F 2-Polimigenyl 1122 1 F 4,6-Dimethoxypolyimidin- 2-yl 1123 1 F 4,6-Dimethylpyrimin-2-yl 1124 1 F 2-Methoxy-4-methylpyrimin-2-yl 1125 1 F 2-Chloro-4-methoxypyrimin-2-yl 1126 1 F 1 , 3,5-Triazine 1127 1 F 2,4-Dimethoxy-1,3,5-triazin-2-yl 1128 1 F 2,4-Dimethyl-1,3,5-triazin-2-yl 1129 1 F 2 -Thiazolyl 1130 1 F 1,3,4-Thiadiazolyl-2-yl 1131 2 F Hydrogen 1132 2 F Methyl 1133 2 F Ethyl 1134 2 F n-Propyl 1135 2 F Isoprofluoro 1136 2 F n-Butyl 1137 2 F Isobutyl 1138 2 F sec-Butyl 1139 2 F t-Butyl 1140 2 F Binyl 1141 2 F Allyl 1142 2 F 3-Buthenyl 1143 2 F 1-Methyl- 2-Prophenyl 1144 2 F 2-Proponyl 1145 2 F 2-Butyl 1146 2 F 3-Butyl 1147 2 F Phenyl 1148 2 F Naphtyl 1149 2 F 2-Bromo-phenyl 1150 2 F 3-Bromo-phenyl 1151 2 F 4- Blomo-phenyl 1152 2 F 2-chlorophenyl 1153 2 F 3-chlorophenyl 1154 2 F 4-chlorophenyl 1155 2 F 2-methylphenyl 1156 2 F 3-methylphenyl 1157 2 F 4-methylphenyl 1158 2 F 2-methoxyphenyl 1159 2 F 3-methoxyphenyl 1160 2 F 4-methoxyphenyl 1161 2 F 2-nitrphenyl 1162 2 F 3-nitrphenyl 1163 2 F 4-nitrphenyl 1164 2 F Benjel 1165 2 F 2-Bromobenzyl 1166 2 F 3- Bromobenzyl 1167 2 F 4-Blomobenzyl 1168 2 F 2-Chlorobenzyl 1169 2 F 3-Chlorobenzyl 1170 2 F 4-Chlorobenzyl 1171 2 F 2-Methylbenzyl 1172 2 F 3-Methyl Nyl 1173 2 F 4-Methylbenzyl 1174 2 F 2-Methoxybenzyl 1175 2 F 3-Methoxybenzyl 1176 2 F 4-Methoxybenzyl 1177 2 F Cyclopropyl 1178 2 F Cyclopentyl 1179 2 F Cyclohexyl 1180 2 F Cycloheptyl 1181 2 F 2-Perigel 1182 2 F 3-Perigel 1183 2 F 4-Perigel 1184 2 F 2,3-Polasolyryl 1185 2 F 2,3,5-Triazolyl 1186 2 F 2-Polimigenyl 1187 2 F 4,6-Dimethoxypolyimidin-2 -Yl 1188 2 F 4,6-Dimethylpolyimidin-2-yl 1189 2 F 2-methoxy-4-methyl-4-imidin-2-yl 1190 2 F 2-chloro-4-methoxy-4-imidin-2-yl 1191 2 F 1, 3,5-Triazine 1192 2 F 2,4-Dimethoxy-1,3,5-triazin-2-yl 1193 2 F 2,4-Dimethyl-1,3,5-triazin-2-yl 1194 2 F 2- Thiazolyl 1195 2 F 1,3,4-Chiazia 2-yl 1196 0 H Hydrogen 1197 0 H Methyl 1198 0 H Ethyl 1199 0 H n-Propyl 1200 0 H Isopropyl 1201 0 H n-Butyl 1202 0 H Isobutyl 1203 0 H sec-Butyl 1204 0 H t-Butyl 1205 0 H-Bonyl 1206 0 H Allyl 1207 0 H 3-Butenyl 1208 0 H 1-Methyl-2-prophenyl 1209 0 H 2-Propenyl 1210 0 H 2-Butyl 1211 0 H 3-Butyl 1212 0 H Phenyl 1213 0 H Naphtyl 1214 0 H 2-bromo-phenyl 1215 0 H 3-bromo-phenyl 1216 0 H 4-bromo-phenyl 1217 0 H 2-chlorophenyl 1218 0 H 3-chlorophenyl 1219 0 H 4-chlorophenyl 1220 0 H 2-methylphenyl 1221 0 H 3-methylphenyl 1222 0 H 4-methylphenyl 1223 0 H 2-methoxyphenyl 1224 0 H 3-methoxyphenyl 1225 0 H 4-methoxyphenyl 1226 0 H 2-nitrphenyl 1227 0 H 3-nitrphenyl 1228 0 H 4 -Nitorphenyl 1229 0 H 1230 0 H 2-Blomobenzene 1231 0 H 3-Blomobenzene 1232 0 H 4-Blomobenzene 1233 0 H 2-Chlorobenzene 1234 0 H 3-Chlorobenzene 1235 0 H 4-Chlorobenzene 1236 0 H 2-Methylbenzene 1237 0 H 3-Methylbenzene 1238 0 H 4-Methylbenzene 1239 0 H 2-Methoxybenzyl 1240 0 H 3-Methoxybenzil 1241 0 H 4-Methoxybenzil 1242 0 H Cyclopropyl 1243 0 H Cyclopentyl 1244 0 H Cyclohexyl 1245 0 H Cycloheptyl 1246 0 H 2-Pyridine 1247 0 H 3-Pyridine 1248 0 H 4-Pyrdigyl 1249 0 H 2,3-Polasoryl 1250 0 H 2,3,5-Triazolyl 1251 0 H 2-Polimydinyl 1252 0 H 4, 6-Dimethoxypyrimin-2-yl 1253 0 H 4,6-Dimethylpyrimin-2-yl 1254 0 H 2-Methoxy-4-methylpyhyl Limin-2-yl 1255 0 H 2-Chloro-4-methoxypyrimin-2-yl 1256 0 H 1,3,5-triazine 1257 0 H 2,4-Dimethoxy-1,3,5-triazine-2-yl 1258 0 H 2,4-Dimethyl-1,3,5-triazin-2-yl 1259 0 H 2-Thiazolyl 1260 0 H 1,3,4-Thiadiazol-2-yl 1261 0 Cl Hydrogen 1262 0 Cl Methyl 1263 0 Cl Ethyl 1264 0 Cl n-Propyl 1265 0 Cl Isoprophyl 1266 0 Cl n-Butyl 1267 0 Cl Isobutyl 1268 0 Cl sec-Butyl 1269 0 Cl t-Butyl 1270 0 Cl Binyl 1271 0 Cl Allyl 1272 0 Cl 3-Butenyl 1273 0 Cl 1-Methyl-2-Propenyl 1274 0 Cl 2-Propoxyl 1275 0 Cl 2-Butyl 1276 0 Cl 3-Butyl 1277 0 Cl Phenyl 1278 0 Cl Naphtyl 1279 0 Cl 2-Promo-phenyl 1280 0 Cl 3-Promo-phenyl 1281 0 Cl 4-chloro-phenyl 1282 0 Cl 2-chlorophenyl 1283 0 Cl 3-chlorophenyl 1284 0 Cl 4-chlorophenyl 1285 0 Cl 2-methylphenyl 1286 0 Cl 3-methylphenyl 1287 0 Cl 4-methylphenyl 1288 0 Cl 2-methoxyphenyl 1289 0 Cl 3-methoxyphenyl 1290 0 Cl 4-methoxyphenyl 1291 0 Cl 2- Nitorphenyl 1292 0 Cl 3-Nitorphenyl 1293 0 Cl 4-Nitorphenyl 1294 0 Cl Benzyl 1295 0 Cl 2-Blomobenzil 1296 0 Cl 3-Blomobenzil 1297 0 Cl 4-Blorobenzil 1298 0 Cl 2-Chlorobenzil 1299 0 Cl 3-chlorobenzene 1300 0 Cl 4-chlorobenzene 1301 0 Cl 2-methylbenzil 1302 0 Cl 3-methylbenzil 1303 0 Cl 4-methylbenzil 1304 0 Cl 2-methoxybenzil 1305 0 Cl 3-methoxybenzil 1306 0 Cl 4-Methoxybenzyl 1307 0 Cl Cyclopropyl 1308 0 Cl Cyclopentyl 1309 0 Cl Cyclohexyl 1310 0 Cl Cycloheptyl Chill 1311 0 Cl 2-Pyridine 1312 0 Cl 3-Pyridine 1313 0 Cl 4-Pyrrol 1314 0 Cl 2,3-Polasolyl 1315 0 Cl 2,3,5-triazolyl 1316 0 Cl 2-Poliminyl 1317 0 Cl 4,6- Dimethoxypyrimin-2-yl 1318 0 Cl 4,6-Dimethylpyrimin-2-yl 1319 0 Cl 2-Methoxy-4-methylpyrimidin-2-yl 1320 0 Cl 2-Chloro-4-methoxypyrimin-2-yl 1321 0 Cl 1,3,5-triazine 1322 0 Cl 2,4-Dimethoxy-1,3,5-triazin-2-yl 1323 0 Cl 2,4-Dimethyl-1,3,5-triazin-2-yl 1324 0 Cl 2-thiazolyl 1325 0 Cl 1,3,4-thiazol-2-yl

[0021]

Table 2 Table 2 Compound No. n X Y 2001 0 F hydrogen 2002 0 F methyl 2003 0 F Ethyl 2004 0 F n-propyl 2005 0 F isophthalic ° propyl 2006 0 F n-butyl 2007 0 F sec-butyl 2008 0 F t -Butyl 2009 0 F Binyl 2010 0 F Allyl 2011 0 F 3-Butenyl 2012 0 F 1-Methyl-2-propenyl 2013 0 F 2-Prophyl 2014 0 F 2-Betenyl 2015 0 F 3-Bethenyl 2016 0 F Phenyl 2017 0 F Benj

[0022]

Table 3 Table 3 Compound No. n X Y R2 3001 0 F hydrogen methyl 3002 0 F methyl 3003 0 0 F ethyl methyl 3004 0 F n-propyl methyl 3005 F isophthalic ° propyl methyl 3006 0 F n-butyl methyl 3007 0 F sec-Butyl methyl 3008 0 F t-Butyl methyl 3009 0 F Binyl methyl 3010 0 F Allyl methyl 3011 0 F 3-Butenyl methyl 3012 0 F 1-Methyl-2-fluorophenyl methyl 3013 0 F 2-Fluoromethyl 3014 0 F 2 -Butenyl Methyl 3015 0 F 3-Butenyl Methyl 3016 0 F Phenyl Methyl 3017 0 F Benzylic Methyl 3018 0 F Hydrogen Ethyl 3019 0 F Methyl Ethyl 3020 0 F Ethyl Ethyl 3021 0 F n-Fluoroethyl 3022 0 F Isofluoroethyl 3023 0 F n-Butyl ethyl 3024 0 F sec-Butyl ethyl 3025 0 F t-Butyl ethyl 3026 0 F Binyl ethyl 3027 0 F Allyl ethyl 3028 0 F 3-Betenyl ethyl 3029 0 F 1-Methyl-2-prophenyl ethyl 3030 0 F 2-Propyl ethyl 3031 0 F 2-Betenyl ethyl 3032 0 F 3-Betenyl ethyl 3033 0 F Phenyl ethyl 3034 0 F Benzen ethyl 3035 0 F Hydrogen n-Propyl 3036 0 F Methyl n-Propyl 3037 0 F Ethyl n-Propyl 3038 0 F n-Propyl n-Propyl 3039 0 F Isopropyl n-Propyl 3040 0 F n-Phtyl n-Phyl F-304 304 F n-Propyl 3042 0 F t-Butyl n-Propyl 3043 0 F Vinyl n-Propyl 3044 0 F Allyl n-Propyl 3045 0 F 3-Petenyl n-Propyl 3046 0 F 1-Methyl-2-fluoro n-Propyl 3047 F 2-Propyl n-Propyl 3048 0 F 2-Butenyl n-Propyl 3049 0 F 3-Betenyl n-Propyl 3050 0 F Phenyl n- Pro-Pol 3051 0 F Bengi n-Pro-Pol

[0023]

Table 4 Table 4 Compound No. n X Y R ³ 4001 0 F hydrogen methyl 4002 0 F methyl 4003 0 F ethyl methyl 4004 0 F n-propyl methyl 4005 0 F isophthalic ° propyl methyl 4006 0 F n-butyl methyl 4007 0 F sec-Butyl methyl 4008 0 F t-Butyl methyl 4009 0 F Vinyl methyl 4010 0 F Allyl methyl 4011 0 F 3-Butenyl methyl 4012 0 F 1-Methyl-2-fluorophenyl methyl 4013 0 F 2-Fluoromethyl 4014 0 F 2-Butenyl Methyl 4015 0 F 3-Butenyl Methyl 4016 0 F Phenyl Methyl 4017 0 F Benzylic Methyl 4018 0 F Hydrogen Ethyl 4019 0 F Methyl Ethyl 4020 0 F Ethyl 4021 0 F n-Propyl Ethyl 4022 0 F Isofluoroethyl 4023 0 F n-Butyl ethyl 4024 0 F sec-Butyl ethyl 4025 0 F t-Butyl ethyl 4026 0 F Binyl ethyl 4027 0 F Allyl ethyl 402 8 0 F 3-butenyl ethyl 4029 0 F 1-methyl-2-propylenyl ethyl 4030 0 F 2-propyl ethyl 4031 0 F 2-butenyl ethyl 4032 0 F 3-butenyl ethyl 4033 0 F phenyl ethyl 4034 0 F benzyl ethyl 4035 0 F Hydrogen n-Propyl 4036 0 F Methyl n-Propyl 4037 0 F Ethyl n-Propyl 4038 0 F N-Propyl n-Propyl 4039 0 F Isoprophyl n-Propyl 4040 0 F n-Phyl n-41 F-Pol Butyl n-Propyl 4042 0 F t-Butyl n-Propyl 4043 0 F Vinyl n-Propyl 4044 0 F Allyl n-Propyl 4045 0 F 3-Petenyl n-Propyl 4046 0 F 1-Methyl-2-Propenyl n-47 40% 0 F 2 -pronyl n-prooyl 4048 0 F 2-butenyl n-prooyl 4049 0 F 3-butenyl n-prooyl 4050 0 F phenyl n -PROPOLE 4051 0 F Bengi n-PROPOLE

[0024]

Table 5 Table 5 Compound No. n X Y R ³ 5001 0 F hydrogen methyl 5002 0 F methyl 5003 0 F ethyl methyl 5004 0 F n-propyl methyl 5005 0 F isophthalic ° propyl methyl 5006 0 F n-butyl methyl 5007 0 F sec-Butyl methyl 5008 0 F t-Butyl methyl 5009 0 F Binyl methyl 5010 0 F Allyl methyl 5011 0 F 3-Bethenyl methyl 5012 0 F 1-Methyl-2-fluorophenyl methyl 5013 0 F 2-Fluoromethyl Methyl 5014 0 F 2-butenyl methyl 5015 0 F 3-butenyl methyl 5016 0 F phenyl methyl 5017 0 F benzyl methyl 5018 0 F ethyl hydrogen 5019 0 F methyl ethyl 5020 0 F ethyl ethyl 5021 0 F n-fluoroethyl 5022 0 F isofluoroethyl 5023 0 F n-Butyl ethyl 5024 0 F sec-Butyl ethyl 5025 0 F t-Butyl ethyl 5026 0 F Binyl ethyl 5027 0 F Allyl ethyl 502 8 0 F 3 -Betenyl ethyl 5029 0 F 1-Methyl-2-propylenyl ethyl 5030 0 F 2-Propyl ethyl 5031 0 F 2-Betenyl ethyl 5032 0 F 3-Betenyl ethyl 5033 0 F Phenyl ethyl 5034 0 F Benzen ethyl 5035 0 F Hydrogen n-Propyl 5036 0 F Methyl n-Propyl 5037 0 F Ethyl n-Propyl 5038 0 F n-Propyl n-Propyl 5039 0 F Isopropropyl n-Propyl 5040 0 F n-Phyl n-41 F-Pool Butyl n-Propyl 5042 0 F t-Butyl n-Propyl 5043 0 F Vinyl n-Propyl 5044 0 F Allyl n-Propyl 5045 0 F 3-Petenyl n-Propyl 5046 0 F 1-Methyl-2-Propenyl n-47 Propyl 0 F 2-Propylene n-Propyl 5048 0 F 2-Butenyl n-Propyl 5049 0 F 3-Betenyl n-Propyl 5050 0 F Phenyl n -Proport 5051 0 F Bengi n-Proport

[0025]

[Table 6] Table 6 Compound No. n X R ⁴ 6001 0 F methyl 6002 0 F Ethyl 6003 0 F n-propyl 6004 0 F an iso-propyl 6005 0 F n-butyl 6006 0 F sec-butyl 6007 0 F t- Butyl 6008 0 F Phenyl 6009 0 F Benjyl

The compound of the present invention can be produced, for example, by the following methods (method A, method B, method C and method D).

In the general formula (I), A is a group --NR.
^{When 3} Y and R ² and R ³ are hydrogen atoms, the compound (Ia) of the present invention can be produced by the following Method A. (A method)

[0028]

[Chemical 11]

[In the formula, X, Y, R ¹ and n have the same meanings as described above. In the reaction formula of the above-mentioned Method A, the compound represented by the formula (Ia) is obtained by reacting the amide of the above formula (II) in the absence of a solvent or in the presence of a suitable solvent with a suitable base, below freezing point- 78 ° C
To the boiling point of the solvent in the temperature range of the above formula (II
It can be produced by reacting with the substituted isocyanate of I) for 1 to 24 hours.

When a solvent is used in this reaction, suitable solvents include, for example, hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; diethyl ether,
Diisopropyl ether, tetrahydrofuran, 1,4
-Ether solvents such as dioxane; ketone solvents such as acetone and methyl ethyl ketone; ester solvents such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethylformamide, dimethylsulfoxide, dimethylacetamide; acetonitrile, water, etc. be able to. Examples of suitable bases include organic bases such as pyridine and triethylamine, and organic bases such as 1,8-diazabicyclo (5,4,0) -7-undecene.

In the general formula (I), A is a group --NR.
^{When 3} Y and R ² is a hydrogen atom, the compound (Ib) of the present invention can be produced by the following Method B. (Method B)

[0032]

[Chemical 12]

[In the formula, X, Y, R ¹ , R ³ and n have the same meanings as described above. Z represents a lower alkyl group or a phenyl group. In the reaction formula of Method B, the compound represented by the formula (Ib) is the compound of the formula (IV) and the substituted amine of the formula (V) in the presence of no solvent or a suitable solvent, under ice-cooling or solvent. It can be produced by reacting in the temperature range of boiling point of 1 to 24 hours.

When a solvent is used in this reaction, suitable solvents include, for example, hydrocarbon solvents such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as dichloromethane and chloroform, diethyl ether,
Diisopropyl ether, tetrahydrofuran, 14-
Examples include ether solvents such as dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, and dimethylacetamide, acetonitrile, and water. it can.

In the general formula (I), A is a group --NR.
^{When 3} Y and R ² is a lower alkyl group, the compound (Ic) of the present invention can be produced by the following Method C. (C method)

[0036]

[Chemical 13]

[In the formula, X, Y, R ¹ , R ³ and n have the same meanings as described above. In the reaction formula of the above Method C, the compound represented by the formula (I-c) is the compound represented by the formula (Ib) without solvent or in the presence of a suitable solvent, using a suitable base. Then, it can be produced by reacting with various alkylating agents in the temperature range of −78 ° C. below freezing point to the boiling point of the solvent for 1 to 24 hours.

When a solvent is used in this reaction, suitable solvents include, for example, hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; diethyl ether;
Diisopropyl ether, tetrahydrofuran, 1,4
-Ether solvents such as dioxane; ketone solvents such as acetone and methyl ethyl ketone; ester solvents such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, dimethylacetamide; acetonitrile and the like. it can.

Suitable bases include, for example, carbonates such as sodium carbonate and potassium carbonate; sodium hydroxide,
Metal hydroxides such as potassium hydroxide; Metal alcoholates such as sodium methylate and sodium ethylate; Alkyl metal hydrides such as sodium hydride and potassium hydride; Lithium diethylamide, lithium diisopropylamide, lithium bistrimethylsilylamide, etc. The lithium amides can be mentioned.

Examples of the alkylating agent include lower alkyl halides such as methyl bromide, ethyl bromide, methyl iodide and ethyl iodide, lower alkyl methane sulfonates such as methyl methane sulfonate and ethyl methane sulfonate, methyl benzene sulfonate and ethyl benzene sulfonate. Lower alkylbenzene sulfonate, such as methyl paratoluene sulfonate,
Examples thereof include lower alkyl paratoluene sulfonate such as ethyl paratoluene sulfonate, methyl trifluoromethane sulfonate, lower alkyl trifluoro methane sulfonate such as ethyl trifluoromethane sulfonate, and di-lower alkyl sulfuric acid such as dimethyl sulfuric acid and diethyl sulfuric acid.

In the general formula (I), A is a group -OR.
^When R ² is ⁴ and R ² is a hydrogen atom, the compound (Id) of the present invention can be produced by the following Method D. (D method)

[0042]

[Chemical 14]

[In the formula, X, Y, R ¹ , R ⁴ and n have the same meanings as described above, and Q is a halogen atom or a group —OR.
^{Shows 4} . In the reaction formula of the above-mentioned Method D, the compound represented by the formula (Id) is the compound represented by the formula (II) without solvent or in the presence of a suitable solvent, using a suitable base, Below freezing −
It can be produced by reacting with the compound represented by the chemical formula (VI) in the temperature range of 78 ° C. to the boiling point of the solvent for 1 to 24 hours.

When a solvent is used in this reaction, suitable solvents include, for example, hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; diethyl ether,
Diisopropyl ether, tetrahydrofuran, 1,4
-Ether solvents such as dioxane; ketone solvents such as acetone and methyl ethyl ketone; ester solvents such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethylformamide, dimethylsulfoxide, dimethylacetamide; acetonitrile, water, etc. be able to.

Suitable bases include, for example, carbonates such as sodium carbonate and potassium carbonate; sodium hydroxide,
Metal hydroxides such as potassium hydroxide; Metal alcoholates such as sodium methylate and sodium ethylate; Alkyl metal hydrides such as sodium hydride and potassium hydride; Lithium diethylamide, lithium diisopropylamide, lithium bistrimethylsilylamide, etc. The lithium amides can be mentioned.

After completion of the reaction, the reaction solution is subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, purified by operations such as chromatography and recrystallization to obtain the desired compound. it can. Next, the present invention will be described more specifically with reference to examples.

[0047]

EXAMPLES Production Example 1 1- [1-fluoro-2- (4,6-dimethoxypyrimyi
Dinyl-2-oxy) -cyclopentanecarbonyl]-
Trans form of 3-methylurea (Compound No. 1002)
Synthesis of; Yo - it was synthesized according to the method described in European patent publication 0,468,766 1- fluoro-2
-(4,6-dimethoxypyrimidinyl-2-oxy)-
Trans form of 1-cyclopentanecarboxamide 0.3
12 g of acetonitrile solution of 5 g (1.23 mmol)
0.15 g of methyl isocyanate (2.63 mmo)
l) and 1,8-diazabicyclo (5,4,0) -7-
Undecen was added. The mixture was stirred at room temperature for 2 hours. The reaction solution was poured into 20 ml of an acidic solution and extracted three times with 20 ml of ethyl acetate, and the obtained organic layer was dried over magnesium sulfate. The organic layer was distilled off to obtain 0.44 g of a composition organism. This was purified by silica gel column chromatography (developing solvent: chloroform / methanol = 50/1), and the desired 1- [1-fluoro-2- (4,6-dimethoxypyrimidinyl-2-oxy) -cyclo was obtained. 0.13 g (yield: 35%) of trans form of pentanecarbonyl] -3-methylurea (Compound No. 1002) was obtained.

Production Example 2 1-Fluoro-2- (4,6-dimethoxypyrimidinyl
2-oxy) -1-cyclopentanecarboxamide
Phenoxycarbamate trans form (Compound No. 6
Synthesis of 008); European Patent Publication 046876.
30 ml of a solution of 1-fluoro-2- (4,6-dimethoxypyrimidinyl-2-oxy) -1-cyclopentanecarboxamide in the trans form (3.7 g, 13 mmole) synthesized according to the method described in No. 6 in dimethylformamide. 0.52 g of 60% sodium hydride (1
3 mmole) was added to 8 ml of a dimethylformamide solution at -5 ° C, and the mixture was reacted for 1 hour. A solution of 2.78 g (13 mmole) of diphenyl carbonate in 13 ml of dimethylformamide was added dropwise thereto at -5 ° C., and the reaction solution was further reacted at room temperature for 4 hours. It was extracted twice, and the obtained organic layer was dried over magnesium sulfate. The organic layer was distilled off to obtain 6.3 g of a composition organism. Silica gel column chromatography (developing solvent: ethyl acetate / hexane = 3)
1), and 2.7 g of the trans form (compound No. 6008) of phenoxy-bamate of 1-fluoro-2- (4,6-dimethoxypyrimidinyl-2-oxy) -1-cyclopentanecarboxamide. 52%).

Production Example 3 1- [1-fluoro-2- (4,6-dimethoxypyrimyi
Dinyl-2-oxy) -cyclopentanecarbonyl]-
3- (4,6-dimethoxypyrimidin-2-yl) ure
Synthesis of a trans form (Compound No. 1057); 1-fluoro-2- (4,6-dimethoxypyrimidinyl-2-oxy) -1-cyclopentanecarboxamide phenoxy-bamate trans form obtained in Production Example 2 ( Compound No. 6008) 0.41 g (1.0 mmol) and 2
-Amino-4,6-dimethoxypyrimidine 0.16 g
A solution of (1.0 mmol) in 10 ml of 1,4-dioxane was refluxed for 2 hours. The reaction solution was poured into 20 ml of hydrochloric acid acidic solution, and the precipitated crystals were filtered to obtain the desired 1- [1-fluoro-2- (4,6-dimethoxypyrimidinyl-2-oxy) -cyclopentanecarbonyl] -3-. (4,6-
0.15 g of the trans form of dimethoxypyrimidin-2-yl) urea (Compound No. 1057) (yield: 33%)
Got

The compounds shown in Table 1 above were synthesized by the same method. Table 7 shows the NMR data of these compounds.

[0051]

Table 7 Table 7 Compound No. NMR (CDCl3) δ ppm 1001 1.71-2.54 (6H, m), 3.9 (6H, s), 5.42-5.72 (1H, m), 5.71 (1H, s) 1002 1.63- 2.72 (6H, m), 2.85 (3H, d, J = 4.6 Hz), 3.84 (6H, s), 5.17-5.78 (1H, m) 5.62 (1H, s), 7.75-8.27 (1H, bs) 1003 1.11-1.28 (3H, m), 2.75-2.52 (6H, m), 3.25-3.36 (2H, m), 3.91 (6H, s), 5.58-5.69 (1H, m), 5.7 (1H, s), 5.78 (1H, bs), 6.48 (1H, bs) 1004 0.95 (3H, t, J = 7Hz), 1.25-2.73 (8H, m), 3.2 (2H, q, J = 7Hz), 3.85 (6H, s ), 5.23-5.82 (1H, m), 5.65 (1H, s), 8.1 (1H, bs) 1006 0.78-2.78 (13H, m), 2.97-3.48 (2H, m), 3.85 (6H, s), 5.2-5.85 (1H, m), 5.68 (1H, s), 8.1 (2H, bs) 1009 1.38 (9H, s), 2.0-2.47 (6H, m), 3.9 (6H, s), 5.51-5.62 ( 1H, m), 5.71 (1H, s) 8.01 (1H, bs), 8.13 (1H, bs) 1011 1.75-2.49 (6H, m), 3.89 (6H, s), 3.92-3.95 (2H, m), 5.15-5.26 (2H, m), 5.51-5.62 (1H, m), 5.7 (1H, s), 5.83-5.92 (1H, m), 8,24 (1H, bs) 1017 2.03-2.52 (6H, m ), 3.84 (6H, s), 5.7-5.64 (1H, m), 5.69 (1H, s), 7.1-7.15 (1H, m), 7.32-7.38 (2H, m), 7.5-7.55 (2H, m ), 8.25 (1H, bs) 1034 1.57-2.7 (6H, m), 3.78 (6H, s), 4.43 (2H, d, J = 5.6Hz), 5.2-5.85 (1H, m), 5.63 (1H, s), 7.23 (5H, s), 8.4 (1H, bs) 1049 0.93-2.72 (16H, m), 3.3-4.1 (1H, m), 3.85 ( 6H, s), 5.23-5.87 (1H, m), 5.63 (1H, s), 8.07 (1H, s) 1051 1.79-2.55 (6H, m), 3.86 (6H, s), 5.53-5.7 (1H, m), 5.68 (1H, s), 7.02-7.07 (1H, m), 7.67-7.84 (1H, m), 8.03-8.06 (1H, m), 8.31-8.33 (1H, m) 8.4 (1H, bs ) 1052 1.78-2.62 (6H, m), 3.82 (6H, s), 5.43-5.56 (1H, m), 5.68 (1H, s), 7.47-7.49 (2H, m), 8.47 (1H, bs), 8,51-8,52 (2H, m) 1056 1.82-2.6 (6H, m), 3.86 (6H, s), 5.6 (1H, s), 5.58-5.7 (1H, m), 7.01-7.05 (1H , m), 8.62-8.64 (2H, m) 1057 1.79-2.65 (6H, m), 3.86 (6H, s), 3.9 (6H, s), 5.58-5.69 (1H, m), 5.63 (1H, s ) 5.74 (1H, s) 1058 1.78-2.64 (6H, m), 2.36 (6H, s), 3.83 (6H, s), 5.54 (1H, s), 5.61-5.73 (1H, s) 6.68 (1H, s), 7.9 (1H, bs) 1064 1.78-2.56 (6H, m), 3.84 (6H, s), 5.47-5.59 (1H, m), 5.67 (1H, s), 6.99-7.0 (1H, m) , 7.47-7.48 (1H, m), 8.58 (1H.bs) 1065 1.7-2.58 (6H, m), 3.83 (6H, s), 5.46-5.59 (1H, m), 5.67 (1H, s), 8.87 (1H, bs), 8.89 (1H, s) 1068 1.38-1.46 (3H, m), 1.68-2.53 (8H, m), 3.48-3.64 (2H, m), 4.17 (6H, s), 5.58-5.75 (1H, m), 5.96 (1H, s), 8.25 (1H, bs), 8.57 (1H, bs) 1069 1.19 (3H, t, J = 7.4Hz), 1.73-2.56 (10H, m), 3.41- 3.6 (2H, m), 4.2 (6H, s), 5.6-5.78 (1H, m), 5.99 (1H, s), 8.33 (1H, s), 8.6 (1H, bs) 1071 0.91 (3H, t, J = 7.3Hz), 1.27-2.25 (12H, m) , 3.18-3.35 (2H, m), 3.91 (6H, s) 5.35-5.48 (1H, m), 5.7 (1H, s), 8.05 (1H, bs), 8.31 (1H, bs) 1076 1.4-2.26 ( 8H, m), 3.82-3.96 (2H, m), 3.92 (6H, s), 5.09-5.2 (2H, m), 5.32-5.49 (1H, m) 5.7 (1H, s), 5.87-5.99 (1H , m), 8.13 (1H, bs), 8.38 (1H, b) 1099 1.43-2.25 (8H, m), 3.89 (6H, s), 4.36-4.55 (2H, m), 5.31-5.49 (1H, m ), 5.69 (1H, s), 7.24-7.34 (5H, m), 8.39 (2H, bs) 1114 1.01-2.25 (18H, m), 3.43-3.75 (1H, m), 3.91 (6H, s), 5.31-5.97 (1H, m), 5.7 (1H, s), 7.95 (1H, bs), 8,25 (1H, bs) 1116 1.48-2.28 (8H, m), 3.9 (6H, s), 5.39- 5.55 (1H, m), 5.68 (1H, s), 7.03-7.05 (1H, m), 7.64-7.72 (1H, m), 8.02-8.06 (1H, m), 8.28-8.3 (1H, m) 8.5 (1H, bs) 1117 1.4-2.3 (8H, m), 3.9 (6H, s), 5.33-5.5 (1H, m), 5.69 (1H, s), 7.42-7.45 (2H, m), 8.48-8.5 (2H, m), 8.56 (1H, bs) 1122 1.46-2.27 (8H, m), 3.85 (6H, s), 3.98 (6H, s), 5.36-5.53 (1H, m), 5.67 (1H, s) ) 5.77 (1H, s) 1123 1.43-1.28 (8H, m), 2.47 (6H, s), 3.84 (6H, s), 5.44-5.61 (1H, m), 5.66 (1H, s), 6.75 (1H , s) 1129 1.45-2.28 (8H, m), 3.9 (6H, s), 5.38-5.55 (1H, m), 5.69 (1H, s), 6.98-6.99 (1H, m), 7.43-7.44 (1H , m), 8.69 (1H, bs) 1130 1.5-2.29 (8H, m), 3.9 (6H, s), 5.38-5.55 (1H, m), 5.7 (1H, s), 8.84 (1H, s) 6002 1.29 (3H, t, J = 7.0Hz), 1. 75-2.56 (6H, m), 3.90 (6H, s), 4.23 (2H, d, J = 7.0Hz) 5.54-5.68 (1H, m), 5.71 (1H, s), 8.31 (1H, bs) 6008 1.8-2.62 (6H, m), 3.91 (6H, s), 5.58-5.81 (1H, m), 5.74 (1H, s), 7.11-7.42 (5H, m), 8.65 (1H, bs) 6009 1.76- 2.58 (6H, m), 3.86 (6H, s), 5.19 (2H, s), 5.53-5.72 (1H, m), 5.68 (1H, s) 7.37 (5H, m), 8.38 (1H, bs)

The compound of the present invention represented by the general formula (I) has herbicidal activity. When the compound of the present invention is used as a herbicide, a carrier or diluent,
Used by mixing with additives and adjuvants by a method known per se, and prepared into a formulation form usually used as an agricultural chemical, for example, powder, granule, wettable powder, emulsion, liquid, flowable agent, etc. . Further, it can be used in combination or in combination with other pesticides such as fungicides, insecticides, acaricides, other herbicides, plant growth regulators, fertilizers and soil conditioners. Especially by mixing with other herbicides, it not only reduces the amount of drug used but also saves labor,
It is expected that the synergistic action of both drugs will broaden the herbicidal spectrum and a synergistic action will lead to even higher effects. As the carrier or diluent used in the preparation, a solid or liquid carrier generally used in agriculture is used.

Suitable solid carriers used in the preparation include clays and talc represented by kaolinite group, montmorillonite group, illite group or apatargite group; diatomaceous earth, magnesium lime, apatite,
Other inorganic substances such as zeolite, silicic acid anhydride, and synthetic calcium silicate; soy flour, tobacco flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose and other plant organic substances; coumarone resin, petroleum resin, alkyd resin Examples thereof include synthetic or natural polymer compounds such as polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, cobal gums, and dammal gums; and waxes such as carnauba wax and beeswax, urea, and the like.

Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, cumene and methylnaphthalene; dioxane, Ethers such as tetrahydrofuran; ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate;
Methanol, n-hexanol, ethylene glycol,
Examples include alcohols such as diethylene glycol, cyclohexanol, and benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, and diethylene glycol butyl ether; polar solvents such as dimethylformamide and dimethylsulfoxide; and water.

In addition, emulsification, dispersion of the compound of the present invention,
Surfactants and other auxiliaries may be used for the purposes of wetting, spreading, binding, controlling disintegration, stabilizing active ingredients, improving fluidity, and preventing rust. Examples of surfactants used may be nonionic, anionic, cationic and zwitterionic, but are usually nonionic and / or anionic. A compound is used.

Suitable nonionic surfactants include, for example, lauryl alcohol, stearyl alcohol,
Compounds obtained by polymerizing addition of ethylene oxide to higher alcohols such as oleyl alcohol; Compounds obtained by polymerizing addition of ethylene oxide to alkylphenols such as isooctylphenol and nonylphenol; Compounds obtained by polymerizing addition of ethyleneoxide to alkylnaphthols such as butylnaphthol and octylnaphthol; Palmitin acid,
Compounds obtained by polymerizing addition of ethylene oxide to higher fatty acids such as stearic acid and oleic acid; higher fatty acid esters of polyhydric alcohols such as sorbitan and compounds obtained by polymerizing addition of ethylene oxide thereto; compounds obtained by polymerizing addition of ethylene oxide and propylene oxide, etc. Can be mentioned.

Suitable anionic surfactants include, for example, alkyl sulphate salts such as sodium lauryl sulphate, oleyl alcohol sulphate amine salts; alkyl succinate dioctyl esters, sodium 2-ethylhexene sulphonate and the like. Sulfonate; sodium isopropyl naphthalene sulfonate,
Examples thereof include aryl sulfonates such as sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzene sulfonate.

Further, in the herbicide of the present invention, for the purpose of improving the properties of the preparation and enhancing the herbicidal effect, polymers such as casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose and polyvinyl alcohol are used. Compounds and other auxiliary agents can be used in combination.

The above-mentioned carrier and various auxiliary agents are appropriately used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the application scene and the like. The content ratio of the compound (active ingredient) of the present invention in various dosage forms thus obtained varies depending on the dosage form.
Usually, 0.1 to 99% by weight is suitable, and especially 1 to 8
Most preferred is 0% by weight.

In the case of powders, for example, the active ingredient compound is usually contained in an amount of 1 to 25% by weight, and the balance is a solid carrier. In the case of a wettable powder, for example, the active ingredient compound is usually 25 to 9
The rest is a solid carrier and a dispersion wetting agent, and a protective colloid agent, a defoaming agent and the like are added if necessary. In the case of granules, for example, the active ingredient compound is usually contained in an amount of 1 to 35% by weight, and the balance is mostly solid carriers and surfactants. The active ingredient compound is either uniformly mixed with the solid carrier or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm.

In the case of an emulsion, for example, the active ingredient compound is usually contained in an amount of 5 to 60% by weight, to which about 5 to 2% is added.
It contains 0% by weight of an emulsifier, the balance being a liquid carrier, optionally with a rust inhibitor. In the case of a flowable agent, for example, the active ingredient compound is usually contained in an amount of 5 to 50% by weight, the dispersion wetting agent is contained in an amount of 3 to 10% by weight, and the balance is water. ,
Preservatives, defoamers and the like are added.

The halogenated cycloalkanecarbonyl derivative of the present invention can be applied as it is to the compound of the general formula (I) or in any preparation form as described above.
The herbicide of the present invention can be applied to the control or control of various weeds growing in paddy fields and upland fields from the time of outbreak to the growing season. The application rate is about 0.001 to 5 kg, preferably about 0.01 to 1 kg per ha as the amount of the compound represented by the general formula (I) (the amount of active ingredient), and the desired weed species and growth. It can be appropriately selected and changed depending on the stage, application place, application time, weather and the like.

Next, several aspects of formulation examples using the compound of the present invention will be shown. "Parts" in the following formulation examples are based on weight.

Formulation Example 1 (Granule) Compound No. 1002 5 parts Bentonite 40 parts Talc 52 parts Sodium lignin sulfonate 2 parts Polyoxyethylene alkylaryl ether 1 part After thoroughly mixing the above, add an appropriate amount of water. The mixture was kneaded and granulated using a granulator to obtain 100 parts of granules.

Formulation Example 2 (Wettable powder) Compound No. 1017 20 parts Diatomaceous earth 60 parts White carbon 15 parts Sodium lignin sulfonate 3 parts Sodium dialkylnaphthalene sulfonate 2 parts The above components are mixed and uniformly mixed and ground with a jet mill. To obtain 100 parts of wettable powder.

Formulation Example 3 (Emulsion) Compound No. 1052 30 parts Xylene 55 parts Cyclohexanone 10 parts Calcium dodecylbenzene sulfonate 3 parts Polyoxyethylene alkylaryl ether 2 parts The above components were uniformly mixed and dissolved to obtain 100 parts of an emulsion. .

Drugs using the compound of the present invention were each prepared according to the above-mentioned preparation examples.

[0068]

The effect of the present invention is represented by the above general formula (I),
The cycloalkanecarbonyl derivative is a novel compound which has not been described in any literature. The compound represented by the general formula (I) of the present invention has an alkanecarbonyl moiety having a halogen atom at a specific position and a pyrimidine ring having a specific substituent bonded to the 4-position and the 6-position thereof is oxygen. It is characterized by the fact that it has a unique structure in which it is bonded via atoms, and it is considered that the excellent herbicidal action is expressed by the structural characteristics.

The compound and the herbicide of the present invention can control various weeds which grow in agricultural land from the pre-emergence stage to the growing season. For example, paddy field weeds such as Nobie, Firefly, Mizuhigai, Konagi, Azaena, Mizohabe, Kishigusa, Matsubai, Urikawa, etc., or Crabgrass, Enocorogusa, Ohishiba, Suzumenohe, Suzumetenopia, Amaranthaceae, Japanese apricot, Japanese scabbard, Japanese apricot, Japanese apricot, Japanese apricot, Japanese apricot, Japanese apricot, Japanese apricot, Japanese apricot, Japanese apricot, Japanese abalone, Japanese apricot, Japanese apricot, Japanese apricot, Japanese abalone, scabbard, Japanese apricot, sardine, sardine, It is possible to control weeds such as morning glory, morning glory, ragweed, ragweed, rapeseed, sedgeweed, sengangusa, yaemgra and buckwheat vine. Furthermore, not only paddy fields and upland fields, but also orchards, mulberry fields,
It can also be used on lawns and non-cultivated lands.

Moreover, the compounds of the present invention have selectivity for certain cultivated crops, and particularly excellent for crops such as cotton, soybean, corn and the like. Next, the herbicidal effect will be described with reference to test examples.

Test Example 1 (Treatment of Upland Field and Leaves) A square pot (30 × 30 × 12 cm) was filled with upland soil, and various crops and various weed seeds shown in Table 8 were sown in fixed amounts, and each plant was It was grown in a greenhouse until the 1.5-3 leaf stage. The compound of the present invention or the compound of the comparative agent shown in Table 8 was prepared into a wettable powder according to Preparation Example 2, and the water dilution thereof was adjusted to 500 so that the amount of the active ingredient shown in Table 8 was obtained.
It was evenly applied to the foliage of each plant at an amount of 1 / ha. Twenty-one days after spraying the chemicals, the herbicidal effect on various weeds and the degree of phytotoxicity on various crops were determined according to the following criteria. The results are shown in Table 8.

[0072]

[Table 8]

[0073]

[Table 9]

Test Example 2 (Soil Treatment Before Germination of Upland Field) A square pot (30 × 30 × 12 cm) was filled with upland soil, and various crops and various weed seeds shown in Table 9 were sown in fixed amounts, and then 1 cm. Covered the soil. The compound of the present invention or the compound of the comparative agent shown in Table 9 was prepared as a wettable powder according to Formulation Example 2, and the diluted solution thereof was applied at an amount of 500 l / ha so as to obtain the amount of active ingredient shown in Table 9. It was sprayed evenly on the soil surface. Twenty-one days after spraying the chemicals, the herbicidal effect on various weeds and the degree of chemical damage to various crops were determined according to the criteria of Test Example 1. The results are shown in Table 9.

[0075]

[Table 10]

Front page continued (72) Inventor Mitsuru Hikido 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Mitsubishi Petrochemical Co., Ltd. Tsukuba Research Institute (72) Inventor Kumiko Tamura 8-chome, Ami-cho, Inashiki-gun, Ibaraki No. 1 Mitsubishi Petrochemical Co., Ltd. Tsukuba Research Institute (72) Inventor Rika Higurashi 83-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Prefecture Mitsubishi Petrochemical Co., Ltd. Tsukuba Research Institute

Claims (2)

[Claims] 1. The following general formula (I): [In the formula, X represents a hydrogen atom or a halogen atom, and R ¹
Represents a methoxy group or a halogen atom, R ² represents a hydrogen atom or an agriculturally acceptable salt thereof or a lower alkyl group, A represents a group —NR ³ Y or a group —OR ⁴ , and (wherein Y represents Is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or in each case a hydrogen atom, a halogen atom, A lower alkyl group, a 5- or 6-membered heterocyclic group optionally substituted with a lower alkoxy group, R ³ represents a hydrogen atom or a lower alkyl group,
R ⁴ represents a lower alkyl group, a lower alkenyl group, an optionally substituted aryl group or an optionally substituted aralkyl group. ) And n are integers from 0 to 3. ] The cycloalkane carbonyl derivative represented by these. 2. The following general formula (I): [In the formula, X represents a hydrogen atom or a halogen atom, and R ¹
Represents a methoxy group or a halogen atom, R ² represents a hydrogen atom or an agriculturally acceptable salt thereof or a lower alkyl group, A represents a group —NR ³ Y or group —OR ⁴ (wherein Y represents Hydrogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, lower cycloalkyl group, optionally substituted aryl group, optionally substituted aralkyl group, or in each case hydrogen atom, halogen atom, lower It represents a 5- or 6-membered heterocyclic group which may be optionally substituted with an alkyl group or a lower alkoxy group, and R ³ represents a hydrogen atom or a lower alkyl group.),
R ⁴ represents a lower alkyl group, a lower alkenyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, and n represents an integer of 0 to 3. ] The herbicide which contains the cycloalkane carbonyl derivative represented by these as an active ingredient.